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Thioglycolic Acid for Discoloration Treatment

12

[ Note from hobby: I split the following 5 posts from the chemical peeling thread. This deserves its own thread.]

Hello,

As a long-time lurker whose found his questions amply answered by the search feature, I haven’t felt the need to contribute. There are many very intelligent posters here with analytical curiosity; most problems aren’t long for the world before solutions are forged from a combination of pointed Internet searches and quick informational breakdown. I’m entirely grateful for this fact.

This problem of discoloration has irked me for quite some time. Like hobby first hypothesized in 2003, my feeling is that hemosiderin is responsible for the more severe and long-lasting discoloration recalcitrant to superficial exfoliation and “healing salves” (arnica, vitamin K, etc.). Of course, to presume all discoloration is the result of hemosiderin deposits ignores the very real possibility of post-inflammatory hyperpigmentation, which forms under similar conditions (damage to capillaries and dermal/epidermal inflammation). With the latter, treatments such as hydroquinone or kojic acid would be effective as the condition is melanin-caused. Unfortunately, hemosiderin is an iron decomposing product and is infamously stubborn to post-operative treatments when it occurs (hemosiderin staining occurs amongst 10-30% of scerlotherapy patients, largely when injecting the sclerosing agent incorrectly into superficial veins). Most of this is well-known, and I’m probably belaboring the obvious.

Hobby’s feeling that the most efficient means of dealing with hemosiderin deposits is medium-depth chemical peeling gels with my train-of-thought. In fact, the only mentioned treatment amongst the very few medical articles referring to hemosiderin staining is medium-depth trichloroacetic acid (TCA) peeling, generally of 10-25% concentration which is sufficient to penetrate to the papillary dermis, hypothesized to be the site of most hemosiderin deposition. Although demonstratively effective thanks to hobby’s exploratory self-trial, this treatment bears a few obvious disadvantages:

1.) It’s painful. While “no pain, no gain” is certainly a justified philosophy when dealing with an aesthetic condition causing sufficient anxiety to warrant suffering through a few minutes of stinging, it’s undeniable a gentle, painless treatment would be preferable (if it indeed exists).

2.) Downtime. Medium-depth peels cause destruction down to the papillary dermis—the uppermost layer of the dermis just below the basal layer of the epidermis—as well as inflammation of the reticular dermis, the middle layer of the dermis comprising most of the skin’s volume. A resting time of 7-10 days is necessary for proper healing, with 3-4 weeks of rest being ideal before subjecting treated skin to minor trauma (at the very least indicative of the trauma caused by PE). This makes a medium-depth peel inconvenient, especially if performed in the midst of active PE.

3.) Inconsistency. Although once thought to be the by-product of the collodion in the wart remover composition, later trials by other members revealed even “pure” acidic compounds (ethyl-based) suffered the hit-or-miss effectiveness of missing patches of discoloration. While errors in burning could certainly be corrected with future burns, all this goes to contribute to the inconvenience of downtime.

Negative aspects aside, when medium-depth peels presented the only viable solution to hemosiderin deposition one could hardly weigh the disadvantages heavier than the benefits. If that’s not obvious enough foreshadowing, there perhaps exists another option:

Http://www.freepatentsonline.com/EP0975321.html

Summary: Using thioglycolic acid in concentrations ranging from .5-30% to remove hemosiderin deposits, specifically after sclerotherapy. If you are looking for the Cliff Notes, the theory is as follows: Thioglycolic acid is a strong attractor of metals; it forms complexes with metal ions when introduced. Given it’s strong affinity for binding, if thioglycolic acid could penetrate sufficiently deep through the epidermis into the papillary layer to bind with hemosiderin, the formed compound could then be more readily eliminated by the body’s waste removal. Since it’s reaction with the skin produces nearly no side effects except in cases of inappropriately-prolonged exposure, it provides a safe and simple solution to the dilemma of hemosiderin deposition.

Or, so the story goes. What instantly set off a red-flag is the fact this information is provided on a “free patent” website; given a proposed product neither confirms nor denies it’s effectiveness by virtue of having been granted a patent, what’s written could simply be hogwash. While such skepticism is certainly justified, I still felt curious; who would argue so stridently for the effectiveness of a chemical/biological interaction for the sake of selling a product? Perhaps that’s best left unanswered.

OK, so perhaps the source isn’t entirely reputable. In any event, the proposed mechanism is safe, and the active ingredient is readily available. Thioglycolic acid is a well-established and effective depilatory, typically present in powered formulations as calcium thioglycolate. What was once (and, from my own experience, still should be) toted on this forum as an effective alternative to pubic shaving, Magic Shaving Powder includes as an active ingredient calcium thioglycolate (in it’s gold and platinum-canned products). My own personal experience: Prior to summer of 2007, I used the platinum Magic Powder for removal of scrotal/shaft hair. Application would often extent upwards to just before the circ scar for the sake of completion. During this period I incurred no lasting discoloration. For comparison, during this time I used fairly vigorous high-erection jelqs and moderate clamping, two exercises which historically often contribute to discoloration. Can I be certain the MSP prevented hemosiderin deposition? Of course not. But, since the intensity of my PE has not increased since then—only the level of spotty discoloration—it is a possibility.

I have now completed two full applications of the platinum Magic Shaving Powder to my penis. This includes the whole penis—even the glans. I do not find any burning nor noticeable pain for the event. Afterwards, the skin on the penis is much smoother, and it works very well as a depilatory; only very sparse stubble remains. The discoloration, thus far, is largely unchanged. Since I have only completed two applications (performed every-other-day), I cannot be sure of it’s effectiveness. My assumption is that chemical complexing is not an instantaneous process as chemical peeling would be, thus requiring either more time or more applications before a noticeable effect could be achieved. I may be incorrect in that assumption.

I will update my progress in this thread, whether there be progress or none at all. I do hope I’m not shifting too far from the initial subject; I just felt this information would best be suited here instead of in another passed-over post on discoloration. If it need be moved, I apologize.

This is the least I can do to give back to a forum which has given so much to me. Although my excursion into the unknown bears none of the risk hobby’s did with his salicylic acid application, I hope it offers some answers all the same. Good luck to all of you!

-Bill

Be sure to read the warnings posted here and here.

Bill,

Thank you for posting about your discovery. This could be really big news.

You’re quite correct that the fact that something is patented doesn’t mean it actually works. But it does mean that somebody had enough faith in the idea to pay lots of money to write the patent application and get it through the different patent offices.

This particular patent application has been filed in several different countries, which would have cost somebody a small fortune. I would assume the idea has promise, although it’s possible that no effective product has yet been developed.

For more information on the patent applications, look here: http://v3.espacenet.com/publication…9847466A2&KC=A2

By the way, the patents on the site that you linked to are only “free” because they don’t charge for downloading information. Other sites do. The “free” designation has nothing to do with the patent applications themselves, so it’s no reason to suspect this particular one.


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Full text of description (from the above link):


THE USE OP THIOGLYCOLIC ACID AS DEPIGMENTING AGENT
The present invention relates to the use of 2mercaptoacetic acid (thioglycolic acid) for the preparation of cosmetic and pharmaceutical compositions having depigmenting activity on skin spots of ferric origin (hemosiderin), which often occur during sclerotherapy or intravenous infusion administrations.

Such spots are present on skin as more or less permanent pigmentations.

Backaround of the invention
The formation of hemosiderinic (ferric) pigmentations on the treated site is a side effect given by all the sclerosing solutions, normally used in therapy. This side effect is quite general and independent from the correct use of sclerosing solutions and the technique of application of sclerotherapy.

Hemosiderinic pigmentations appear in the form of dark cutaneous spots, which are felt as a serious aesthetic damage by patients, who consequently do not normally comply with this kind of therapy. These inconveniences are more frequent in small blood vessels, such as telangiectasis, which notoriously represent 802 of sclerotherapic applications. According to some Authors (M.P. Goldman, USA), the incidence of these postsclerosis hyperpigmentation is estimated about 10-30 % of the patients undergoing sclerosing therapy independently from the type of medicament used.

Most of all, prevention of hyperpigmentation is obtained by applying a correct sclerotherapeutic technique, by selecting the appropriate type and doses of sclerosing agent. However, notwithstanding the above measures, these side effects may happen even to the most expert sclerotherapist.

Accordingly, the availability of a cosmetic or pharmaceutical agent capable of eliminating or at least reducing this aesthetic damage is still today strongly desired by the therapist and patients.

Among the several preparations having depigmenting activity, the so-called hemosiderinic solubilizing agents, for topical use, have proven to be effective and do not show undesirable side effects. These are preparations normally of cosmetic adjuvants able to “solubilize” hemosiderin.

Post-sclerotherapy pigmentations form in about 6-12 weeks from the end of therapy; they have a linearmacular morphology with a grey to dark brown colour.

Generally, colouring tends to brown in the course of some years, except in case of spontaneous resolutions.

A number of scientific proposals has been offered to explain the genesis of these pigmentations, but only in the last 20 years, experimental evidences of their exact nature have been obtained, thanks to bioptic studies of some Authors (Barner, 1977; Cuttel and Fox, 1982; Goldman, 1987) who demonstrated the almost exclusively haematic origin of the pigment associable with the protein complex called “hemosiderin”.

In particular, Goldman (J. Dermatol. Surg. Oncol., 13,547.1987) studied the effect of the pigmentation genesis in patients subjected to telangectasic therapies (small blood vessels) using different agents in different conditions.

The essentially “haematic” nature of the “postsclerotic” pigmentation was therefore widely demonstrated.

Hemosiderin, which is a base component of pigmentation, forms from the degradation of haeme in the cycle of bile genesis, and has different morphologies of complex nature, as shown by some studies (Richter, 1957 e 1965; Shoden, 1960; Wells, 1962). Genesis cycle, during sclerosing therapies, can be summarized as follows: - sclerosing action determines erhytrodiapedesis, due
to the combined effect of needle shock and
alteration of blood vessel permeability: hence the
subsequent degradation of haemoglobin in the
tissue-site; - consequently, there is complexation with
apoferritin part of the iron released from haeme
and formation of the ferritin protein complex,
which represents the mobile and hydrosoluble pool
of ferric storage in physiological environment; - the subsequent degradation to hemosiderin, which is
insoluble in aqueous environments, can be explained
by the action of acid environment (often given by
sclerosing solutions themselves, which have acidic
pH) and a further degradation of ferritin and loss
of the protein part apoferritin. The hemosiderin
complex is water-insoluble, except at very low pH,
thus allowing the organism to have available an
“iron pool”, which is released only in particular
pH conditions.

Therefore hemosiderin would be a sort of biological advantage, because, on one hand, it would release iron only in particular conditions (pH < 4.5) as shown by O'Connel (1986, Biochem. J., 234:727-731) and, on the other hand, it would avoid the presence of free iron, which is known to be toxic.

Taking into account what above discussed, in the topical treatment of epidermal spots, one should distinguish the goal of reducing and eliminating pigmentations of melanine origin, which earlier patents relates to (South Africa patent n. 68-3773), with respect to the goal of reducing and eliminating pigmentations of haematic origin, in particular those of hemosiderinic genesis and coming from sclerotherapy and intravenous infusion treatments (blood transfusions, etc.). Reduction and elimination of skin pigmentations of haematic origin, in particular those of hemosiderinic genesis and coming from sclerotherapy and intravenous infusion treatments (blood transfusions, etc.) is the problem faced by the present invention.

As above said, contrary to ferritin, the protein complex containing trivalent iron is insoluble and accumulates in dermis permanently (particularly in papillar dermis) showing a characteristic brown spot, with remarkable unesthetic effect.

In previous years, a number of techniques, believed to be suitable to solve such essentially unaesthetic inconvenience, were proposed.

As a matter of clarity and better understanding, these techniques may be classified in instrumental techniques and in techniques using substances having physico-chemical activities.

Main instrumental techniques are the following 1. Crvotherav: it is a complex and expensive
technique, which has the intrinsic difficulty of
determining the exact deepness of frozing.

2. Dermo-Microabrasion: consists in the use of vacuum
systems with mineral powders (Corundum). It gives
variable results and is expensive.

3. Laser systems: two expensive kinds of apparatuses
are available, but variable and not reproducible
results are obtained.

Chemical substances having depigmenting activity can be divided in two classes: 1. Substances having chelating action on hemosiderin
iron; 2. Substances having solubilizing action on
hemosiderin.

Both classes are used in topical formulations.

In the first class ethylenediaminotetracetic acid (EDTA) is found; it shows the well-known chelating effect on metals and is used in formulations having 15% concentration (150 mg/ml).

Further, desferroxamine is a hydrosoluble sideramine capable of chelating iron ion specifically.

It is used topically, but the results are not reproducible.

Among the solubilizing substances of the second class, the following are mentioned: - alfa-hydroxyacids, in particular 2-hydroxyacetic
acid (glycolic acid). This substance does not have
a constant effect in its results because it is not
capable of reaching the derm and, in order to
obtain a medium effect, it requires the application
on epidermis for very long times.

Plurihalogen acids. In particular trichloroacetic
acid is mentioned, because it has a very good
penetration capability in the cutis and can easily
reach hemosiderin and solubilize it, due to its
characteristics of very strong acid. But occurrence
of side effects, such as hypopigmentations and
post-phlogosis scars from chemical burning are
reported. Also incidents of activation of
keratocytes of the basal layer and reduction of the
basal melanophores are reported. Normally,
trichloroacetic acid is used in aqueous or
amphiphilic solutions, with concentrations ranging
from 10 to 40%.

Examining in detail the simplest and less expensive techniques, which are those using cosmetic or pharmaceutical formulations having a solubilizing action, the person having ordinary experience in the art will ascertain some drawbacks that, in one way or in another, lower the efficacy or makes their use difficult. In fact, taking into account what above stated, it can be said: - the use of formulations containing chelating
agents, such as EDTA or desferroxamine (already
proposed by some authors, see Meyers in 1966 and
Goldman in 1992) give variable, uncertain results,
likely due to their difficult diffusion through
cutis, since topical way is the most preferred; - the selection of solubilizing substances unfortu
nately comprises other kinds of problems. Trichlo
roacetic acid, although highly effective, is
dangerous because it is a strong acid and has a
strong protein denaturating activity: even if it
used at low concentrations or for short periods of
time (but in this case efficacy is lowered), it
gives rise to phlyctena, hypopigmentations due to
melanocyte destruction. On the contrary, the choice
of using preparations containing glycolic acid does
not show these noxious effects, since it is not a
strong acid, as trichloroacetic acid is, but it has
a very superficial activity, as it cannot easily
penetrate the epidermic-dermal junction: in order
to reach the miminum efficacy, very long
application times are necessary. But in this case,
side effects similar to those experienced with
trichloroacetic acid occur, for example
hypopigmentation. Accordingly, a correct and
cautious use gives only variable results.

For the reasons above discussed, the therapist is still looking for a highly effective active ingredient without exposing the patient to the risks or problems encountered in the present state of the art.

Summary of the invention
It has now surprisingly been found that 2mercaptoacetic acid (commonly named “thioglycolic acid”) shows a strong and exceptional depigmenting activity and gives constant results. Advantageously, many side effects, arising from the use of the active ingredients of the art, do not appear when 2-mercaptoacetic acid is used.

Accordingly, it is an object of the present invention the use of 2-mercaptoacetic acid as active ingredient for the preparation of a cosmetic and pharmaceutical composition having depigmenting activity on skin spots of ferric origin.

It is another object of the present invention, a method for the cosmetic treatment of depigmentation of skin spots of ferric origin comprising the application on epidermis of a composition containing 2mercaptoacetic acid.

The inventors do not wish to be bound to any theory, however they believe that the strong solubilizing activity at dermis level with respect to hemosiderin iron is due not only to the acidic characteristic of the active ingredient, but, above all, to the presence of -SH group, which gives the molecule a strong affinity for iron ion in the skin: then, according to the present invention, there is the advantageous result to achieve both the solubilizing effect and the complexing effect with a single active ingredient.

The present invention offers the art of sclerotherapy a number of advantages, because, other than a well established and constant efficacy, the composition is endowed with a high safety of use.

- Only very short application times are required, at
most a few minutes, and it is subsequently elimina
ted with washing and neutralization with a buffer
or simply by washing the treated site with tap
water. Short application times allow to eliminate
risks and dangers of harmful effects, such as
erythemas, phlyctena, hypopigmentations, etc.

- It has also been found that the strong affinity for
iron ion of 2-mercaptoacetic acid gives it a beha
viour similar to that of apoferritin, therefore it
can bind to hemosiderin even at low concentrations,
thus giving higher efficacy at concentrations lower
than those of glycolic acid (used at 7%) and tri
chloroacetic acid (used at 20-40%).

It has further surprisingly been found that thioglycolic acid gives cutis a “rejuvenating” effect.

Therefore, it is another object of the present invention the use of 2-mercaptoacetic acid for the preparation of a cosmetic composition having antiageing activity. Also a cosmetic treatment of skin ageing is within the scope of the present invention.

Once again, the inventors do not wish to base the invention on any theory, but also in this case, the antiageing effect might be explained by the easy grade of oxidation of 2-mercaptoacetic acid, then it is likely that it interacts with free radicals.

2-mercaptoacetic acid was used as chemical reagent in laboratory for the determination of hemosiderin and characterization of its structure and chemical composition (Shoden and Sturgeon in Hemosiderin; Acta Hematol., 376-392, 1960).

Other Authors showed the capability of 2-mercaptoacetic acid of eliminating iron accumulations from spleen and to have antioxidant activity (due to -SH group), for example demonstrated by its presence of metabolite of carboxymethylcysteine. (Joo et al.,
Biol. Met. 3(34), 1715, 1990; Hofman et al., Drug.

Metab. Disps., 19(1)22-6, Jan-Feb. 1991).

Efficacy of 2-mercaptoacetic acid is due only to its characteristic of being simply an acid: in fact it has an acidity definitely lower than the one of trichloroacetic acid (a well known depigmenting agent) (see Table 1 below), in fact 2-mercaptoacetic acid is a midstrenght acid, such as glycolic acid, and as the latter, slightly stronger than acetic acid.

Therefore, the present invention provides an active ingredient, which, although highly effective, does not give side effects. Topical use of the compositions containing 2-mercaptoacetic acid, according to the present invention, does not cause burning or erythema except rare cases, but of very low intensity; also sensitization is quite exceptional and temporary.

Table 1 - Acidic strenath
Substance Chemical formula DKa value
Acetic acid CH3COOH 4.76
Glycolic acid HO-CH2COOH 3.83
Tioglycolic acid HS-CH2COOH 3.68
Chloroacetic acid Cl-CH2COOH 2.85
Trichloroacetic acid Cl3CCOOH 0.70
Pharmaceutical and cosmetic compositions containing 2-mercaptoacetic acid as active ingredient are a further object of the present invention. Said compositions fulfill the scope to provide the phlebologist suitable means for an effective cosmetic or therapeutic treatment without contra-indications with the scope of eliminating or at least minimizing side effects of hemosiderinic pigmentations during sclerotherapy treatments.

According to the present invention, 2-mercaptoace tic acid shall be used in an amount higher than the minimum value of 3% by weight, thus providing a very effective therapeutical means, that in any case is to be used in a treatment in casualty department.

Compositions having definitely lower concentrations (lower than 3% by weight), are foreseen for a possible continuation of the treatment at home, in order to establish an effective maintenance treatment.

Generally, the effective amount of active ingredient is comprised from 0.5 to 30% by weight. This range of concentration is also useful to be used as an antiaging tool.

According to the present invention, the cosmetic composition containing 2-mercaptoacetic acid shall have a pH of the aqueous base ranging from 2.5-7.0, by adjusting the aqueous solution either with basic agents (sodium, ammonium or potassium hydroxide solution) or with mixtures of suitable buffer salts (sodium or potassium phosphate salts).

The compositions according to the present invention are preferably in the form of hydro-alcoholic solutions or gels or ointments.

The preparation of the compositions can be carried out according to conventional techniques well-known to the skilled person.

As an example, methods for industrial manufacture are disclosed below: 1. Solutions having concentrations comprised in the
0.5-15% w/w range in 20 ml bottle and/or 2 ml am
poules.

2. Ointments and/or gels having concentrations compri
sed in the range 0.5-15% w/w in 20 g tube and/or 3
g sachets.

Example 1
Formulation for the preparation of 1000 g of 12% solution, in 20 ml bottles and/or 2 ml ampoules.

Startina materials Amounts aramiKa
12t solution
Thioglycolic acid 100% 120
Ethyl alcohol 96” 200
Polyethylene glycol 400 200
Antioxidant 1.00
Perfume 20
Water : q.s. to 1000 grams.

In a glass vessel, equipped with stirrer, ethyl alcohol is mixed with polyethylene glycol till complete dissolution; antioxidant, then thioglycolic acid and perfume are slowly added while stirring.

Depurated water is added under stirring to the final weight in order to have a complete dissolution.

The mass is filtered, if necessary, through membrane and used for primary packaging by means of an equipment with automatic control of the distributed quantity.

Moulded glass bottles, having brown colour for light protection, are used.

Class I-glass ampoules are packaged in normal conditions, since the solutions are not for injection: ampoule filling is carried out in nitrogen atmosphere, having previoulsy purged the ampoules with nitrogen, to preserve the best stability during the time.

Example 2
Formulation for the preparation of 100 grams 12 % of ointment and/or gel in 20 g tube and/or in 3 g sachets.

Starting Amount in grams for Component materials 12% ointment/gel characteristics
Mercaptoacetic acid 12.0 Aqueous phase
Glycerine 4.0 Aqueous phase
Xanthan Gum 2.0 Aqueous phase
Brij 721/72 5 Emulsifying
Cetyl/stearyl alcohol 3.0 Fatty phase
Cetiol V 4 Fatty phase
Isopropyl myristate 3.0 Fatty phase
Titanium dioxide 2.0 Solid phase
Tocopheryl acetate 1 Antioxidant
Perfume 0.2 Hydroalcoho
lic Phase
Preserved water q.s. to 100 grams Aqueous phase Fattv phase: All the fatty materials are placed in a
suitable vessel and melted at the
temperature of 60-70”C, keeping the mass
under stirring.

While stirring, emulsifying agent (Brij), tocopheryl acetate and titanium dioxide are added to the molten mass; subsequently, temperature is lowered to about 50”C.

Aqueous phase: In a similar manner and into a second
suitable vessel, glycerine and the active
ingredient (mercaptoacetic acid) are
dissolved in water keeping the mixture
under continuous stirring, until complete
dissolution. Perfume is added, then the
mass is warmed to about 50”C.

The aqueous phase is subsequently percolated into the fatty phase, kept under stirring with the usual technique for the preparation of oil/water emulsions, cooled down to a temperature such that to maintain the fluidity necessary for the subsequent filling phase in the primary packaging, which can consist of tubes (plastic or metal) or sachets of polycoupled material.


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ModestoMan,

Thanks for pointing out that “free patent” doesn’t mean “free application,” but instead “free viewing.” My inference was based upon free domain name registration services, whose numbers were many during the “.com” bubble. Interesting about the international application filing; I had no idea patent application was so expensive! It certainly goes some way towards convincing one of the idea’s legitimacy.

I applied the Magic Shaving Powder the evening of the 23rd and 25th. For the sake of complete disclosure in the event someone else might want to test this method, my treatment conditions are as follows:

Dispense the powder into a container and mix with water, starting with little water and adding to the mixture in small increments. The step-wise addition of the water is to ensure the resulting paste is as concentrated as possible while still having low enough viscosity as to both be spreadable and absorbable. I apply the paste to the entire penis from base to tip, making sure the layer of paste is thick enough to provide more than adequate substance for absorption. I also apply to the scrotum, but only for the purpose of depilation. I leave the paste on for ten minutes, making sure to dab any area that dries with wet fingertips so that absorption may occur during every moment of application. Once ten minutes is up I rinse myself in the shower with warm water and wipe the paste from my genitals, afterwards going over the entire treated area with a slightly abrasive exfoliating cloth. Manual exfoliation is intended only to remove stubble rinsing did not and clear the hair follicles to avoid ingrown hairs. Whether or not exfoliation is integral to thioglycolic acid’s (TGA) utility in this matter is open to question, but since TGA has mild exfoliating properties in addition to it’s chelating activity I find no reason not to aid with a bit of manual exfoliation as well. While it’d be terrific to pinpoint precisely what may work, I can’t lie: results are paramount to scientific clarity. :)

It would also be worth noting I have continued PEing throughout this treatment. In addition to hating the idea of losing growth and deconditioning to a level where my propensity to discolor may *increase*, I don’t want to risk any improvement being due to rest. So often posters have noted improvement after a week(s) of applying things such as vitamin K creme, 10% glycolic acid lotions or arnica. Unfortunately, the fact they discontinued PEing at the start of treatment makes unclear what should be given credit for any improvement. To be precise, I perform 150 three-second wet jelqs at 85-95% erection in the morning and 300 wet jelqs of the same variety in the evening—six days a week.

After four treatments I believe I’ve seen a bit of improvement. Extremely skeptical as I am, I interpret the effect to be largely a matter of flushing from irritation; either that, or wishful thinking! What cannot be disputed, though, are the 1.5 inches in erect length and over half-inch of girth I’ve added after 5-6 months of very diligent wet jelqing. I know that’s not applicable to the matter at hand, but reading such evidences was always something that kept me faithful all my years of lurking. Thank heavens I have something to show for my efforts besides hemosiderin. :)

So as not to hijack the thread with play-by-play details akin to a progress report, I’ll post in this thread from this point forward only to report either great improvements or complete failure at the endeavour’s end. —Oh, and to respond to any questions, as I’m sure I’ve ignored many details. Good luck everyone, and thanks for your interest, Modesto; it’s surreal to finally interact with the very posters I’ve venerated for years in silence!

Talk to you later,

Bill

Post anytime, Bill. I’ve still got some discoloration left, especially on my glans. Not wanting to burn my glans, I’m really hoping that this works out!


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Interesting info, zarathustra. As MM said, please continue posting. This may turn out to be a good approach to solving the discoloration problem.

I wonder what effect the other ingredients in Magic Shaving Powder may have. Is pure thioglycolic acid available in small quantities?

MM and hobby,

Thanks for the responses! I appreciate the move into a separate thread if not only for the fact I’ll need not feel guilty of hijacking the other, but also because you think it may be warranted.

I’m quite happy to confirm, then, that our faith may be well-placed: the discoloration has noticeably reduced. As of today I have applied Magic Shaving Powder (MSP) eight times. In my previous post I reported that after four applications I possibly saw improvement; if my confidence could have been quantified as a percentage, I’ll say it was 30%. Now, after eight applications, that number is 90%+! Two days after my previous post I noticed a particular patch of discoloration had seemed to lighten considerably from the last time I had checked it (To be precise, about 9 hours before—how obsessed do we sometimes become?) Although my theory of thioglycolic acid’s (TGA) function still leans towards gradual improvement instead of immediate change, a la medium-depth chemical peeling, this change seemed to come about rather suddenly, something akin to spotting a blemish on your forehead that had just the previous night not existed. As we so often catalog the topography of our penises’ coloration and unique features to a degree others would see as, well, totally insane, this particular patch of discoloration was especially dark, having formed roughly three months ago after exceeding my own recommended maximum pressure in a pump. If prior to the four MSP applications the darkness could be ranked 10, it was now 4: a significant and obvious difference!

Since that surprising (and welcome!) discovery I have performed four more applications of MSP. It still maintains it’s distinction as superb superficial exfoliant and depilatory. The scattered groups of discoloration, each possessing a namesake referencing the offending act (“overpump 1, overjelq 3, etc.) have continued to lighten, particularly those on the top of my penis near mid shaft. Experience has shown us that topical treatments vary considerably in their penetration and subsequent effectiveness, although the reasons are not always clear; while skin thickness, surface pH and oil occlusion are all terrific hypotheses, it’s not entirely evident. Nevertheless, TGA also seems to play “favorites.”

Hobby: I’m glad you inquired about the other ingredients in MSP. Always looking to be as precise as possible for the sake of clarity, certainty and care (Experimenting with my penis? Really?), I did a moderate amount of research on any additional ingredient with which I was unfamiliar. I was particularly concerned with eliminating the potential for both an antiplatelet or melanin-sensitizing effect, as both would be extremely counterproductive (Antiplatelet for increased bleeding and potential hemosiderin deposition, melanin-sensitizing for hyperpigmentation [although I don’t nude sunbathe. Limited concern.]). My ingredient reference (besides the can I own): http://www.cosmeticsdatabase.com/pr…p?prod_id=61651

A few ingredients are instantly recognizable and unwelcome: tocopheryl acetate (vitamin E) has a well-documented mild antiplatelet effect—thus it’s popularity for treating heart disease—, coconut oil, castor oil, mink oil and corn oil are all comedogenic, and fragrance always brings the possibility of skin irritation or allergic response (particularly in cheap products, where the fragrance is most crude). Further research revealed that calcium hydroxide had anti-microbial properties, useful if applying MSP in the presence of any cuts/abrasions. It is also strongly basic, though in this particular formulation unlikely to burn due to it’s quantity. Aloe extract is antibacterial and, although in contrast to it’s usual depiction as a moisturizing agent, quite drying in my experience. Retinyl palmitate is a derivative of vitamin A, a substance that, while quite irritating to the skin in certain forms (see moderately effective topical acne treatment Retin-A), is innocuous in this specific formulation. Propylene glycol is a common moisturizer and humectant, one of the product’s truly harmless and beneficial ingredients. Polyquaternium 10 produces an anti-static effect and smooths hair’s outer scales; this is very important, especially in a product designed to remove said hair.

It’s difficult to ignore the 10/10 score the product earns from the website’s hazard classification. Scrolling down the website linked above features a list of each ingredient in descending order—most deadly to least deadly. BHA seems so virulent it may kill off the other 23 letters. Needless to say, most of the cautioning seems speculative, predicated on studies that, while certainly carried out in earnest, are not yet canon. In other words, I’m willing to risk it (At least it gives the feeling of braving some danger. That’s right, hobby: Did you experiment with something that might have given you—erhm—endocrine disruption!) :)

TGA is available for purchase in near-pure formulations; near-pure, as supposedly “At room temperature, concentrations over about 70% in water tend to form 1-2% thioglycolides per month which hydrolyze to the original free compound when made acid or alkaline.” (Source: http://www.sigmaaldrich.com/catalog…=0&QS=ON&F=SPEC). That website allows the purchase of 50, 100, or 500 milliliter sizes of TGA; unfortunately, purchases can only be performed by customers/businesses previously verified to use chemical products (Source: https://www.sigmaaldrich.com/webapp…w?storeId=11001). I have already made the mistake of placing an order prior to that understanding, and many weeks later am still awaiting a refund to my checking account. Given my search has been far from exhaustive, there may exist a better source for TGA. Everyone, please link if you find one!

Roughly three-and-a-half weeks into my trial, I am 90%+ certain this is a relatively painless, fiscally prudent and, given enough time and treatment, very effective alternative to the demonstrably efficacious medium-depth peel. I highly recommend others give it a shot; of course, I have to first offer a few words of watchfulness. As the product’s container reads, do a patch test on similarly constructed skin prior to dousing your goods in total. I’m only one person; what’s tolerable and effective for me may liquify you and cause pain to relatives long since deceased. Although the skin on the penis is singularly sensitive and thin—save for perhaps the eyelids—I find testing products on the skin near the throat, just under the adam’s apple, to be similar in both qualities. If you’re concerned of visibility should irritation occur, the inside of the forearm is also a viable option. Neither of those recommendations were established by medical instruction, only personal experience. Should you find any tingling and burning, if it’s minor enough you feel no need to vocalize or count the seconds in torture I suggest you stick it out. The directions on the can state to leave the product on no more than 7 minutes (Manufacturer recommended 5-7 minutes), but I always left it on for ten minutes. The only rationale I applied was a desire for ample penetration and effectivity. While my first forays into chemical depilation using the MSP brought burning, all experiences after the first week or so were free of nearly any sensation, beyond perhaps a subtle “cooling” effect (Present even now towards the latter half of application). Your mileage may vary; be vigilant!

As always, I’ll return to post anything of salience that crosses my mind. In addition, fire my way any questions you may have; fastidious though I’ve tried to fashion my methodology, god knows I’ve left many things out. If TGA truly happens to be hemosiderin’s silver bullet, think of all the implications! Discoloration, almost always unavoidable at a level of intensity strong enough to affect enlargement, needn’t be a worry; Hobby’s unequivocal discovery gave me such a feeling. Regrettably, given the downtime and inconsistency of any peel strong enough to burn to hemosiderin’s depth it makes little sense to begin one’s chemical peeling venture prior to ending their active PE career. While keeping the efficacy of the method in mind over the course of your PE career may inspire confidence, the amount of anxiety and uncertainty a discolored dick can bring can be great. Reactions vary; some, like Bib, engaged in extremely intense PE, costing them sometimes severe discoloration in their quest for growth. By his own admission it bothered him negligibly, if at all. Alternatively, others like huff found the passion to PE untenable when faced with the prospect of discoloration, especially when it came easily and unaccompanied by growth. I fell somewhere between the two camps; while I was prepared to endure a few years of discoloration in return of a bigger cock, imagining that every sexual encounter from now until I reached my goal could possible suffer by sight of a marbled penis wasn’t welcome. End of the world? No. Worth a few errant Google searches to avoid? Absolutely.

I pray this is the answer: Magic Shaving Powder, platinum can, left on for ten minutes while ensuring moisturization and rinsed off with water, repeated as often as every 36 hours. Let us know how it goes! :)

Bill


Last edited by zarathustra : 08-09-2009 at . Reason: vB code mistakes.

Thanks Bill for the followup! I’m a couple of days into my second application of wart remover, and would love to try your technique once It’s completed it’s cycle.

Bill,

Another brilliant post. Thank you. If this works as well as you hope, you will without question win the prize for the most significant transfer of knowledge to Thundersplace in the fewest number of posts :D .

Have you tried the MSP on your glans? Do you have any special precautions in that regard?


Enter your measurements in the PE Database.

Bill,

I cannot tell you how excited I was when I first read your post in the “Shedding the Snake” thread. For a while now, I’ve been looking for a way to remove the hair the creeps up my shaft while avoiding unsightly and sometimes painful razor burn and ingrown hairs. I’ve also been mulling over which route to take to get rid of the discoloration that has sprung up from jelqing and clamping. I never dreamed that the solution for both annoyances would come in one package! I went out to the store today and bought the Blue Magic Shaving Powder and give it a try. Here is what I’ve found so far.

First off, I wasn’t exactly sure which product you had used in your experiments. You mention the platinum package, which is the scented variety that is available. But in your original post, you also said that the fragrance was an additional ingredient that you would rather have avoided, so I opted for the blue package. For everyone’s information, there is also a Red Magic Shaving Powder, which is the same product but is “extra strength.” I’m not exactly sure what makes it extra powerful, but I erred on the safe side and went with the regular figuring that at $3.00/container, if the blue wasn’t enough, I could manage the future expense of purchasing the red. In the past, I have tried other depilatory creams like Nair and Veet and have always been extremely disappointed by how ineffective they were at removing pubic hair. I have thick, dark, and coarse hair and it always seemed to me that those products really only worked well for people with lighter, or at least thinner hair. I’m happy to say that MSP did the trick. I realize that this is not the topic of this thread, and I want to stay on topic, so I will be brief. MSP was significantly more effective at removing my shaft hair than any other product I’ve tried and I look forward to using it again in the future. Here’s how I went about the process.

I spooned out approximately two tablespoons of the powder into a plastic drinking cup and slowly added cool tap water while mixing until the concoction became a paste that was slightly runny yet viscous enough to stay put upon application. Once the paste was ready, I sat on the edge of my toilet and with my left hand, grabbed just under my glans and stretched my penis slightly. I maintained this stretch for the duration of the treatment. Meanwhile, I applied the paste to my shaft, from the base to just under my glans (I wasn’t ballsy enough to try using it on my head yet. Maybe next time). At first there was a cool, almost menthol sensation, which eventually turned into a mild burning. Nothing that was painful at all, but enough to make me watch the clock very closely as not to leave it on too long. I, too, decided that I would remove the paste after 10 minutes, so when my time was up, I scraped everything off going against the grain of the hair. Now, the package recommends using a “spatula” for removal, so I used a dull plastic knife. I would not recommend using the same because, although the knife was dull, it was also serrated and left groove marks along my shaft, so next time I will use something with a flat edge. However, the groove marks were not deep scratches, but more like the red marks you get from having your back scratched, and about an hour later they were gone. After scraping the product off, I hopped in the shower for a final rinse and used a washcloth to buff the treated area and remove any remaining stubble. I then dried off and applied some Neosporin for good measure. I don’t think that was absolutely necessary, but I thought it could only be beneficial so I went with it.

While my shaft is now clear of hair, after one use it is impossible for me to tell if MSP has cleared up any of my discoloration. I did not anticipate seeing this result immediately, so this is not troubling to me in the least. I can, however, support the statement that the treated skin feels softer than before. I will re-apply most likely on Monday, and will give an update at that time. Meanwhile, if anyone has any questions at all, please feel free to ask away.

Bill, thank you very much for your contribution and I look forward to hearing how things progress for you, too.


"This is my boomstick!"

I hope someone trying this will use it on only a portion of the shaft and leave some discoloration untreated as a control. Otherwise, results may be hard to determine. Pictures may also help, but changes in lighting, looseness of the skin, whether the skin is flushed with blood or not, etc. can cause the same degree of hemosiderin staining to appear differently. If you take pics try to keep the conditions as identical as possible.

Several times I thought something might be working only to later discover I had been fooling myself. Hemosiderin stains are most apparent when the shaft skin is palest and most wrinkled (like after swimming in cold water). Anything that irritates the skin can cause it to become, and perhaps remain if the treatments are repeated often enough, slightly redder/pinker from increased blood flow, disguising the stains somewhat.

If, and only if, discolouration is in fact caused by medium depth hemosiderin staining, as opposed to posttraumatic hyperpigmentation of the melasma type (which would also have been treated by the chemical peeling), then what’s to say that just leaving some calcium thioglycolate on the surface of your skin for ten minutes is going to be able to penetrate through to the papillary layer to bind with the relevant metal ions?

The other potential disadvantage of the method is that it can only treat discolouration caused by hemosiderin staining, whereas, to me, at least, it seems far more likely that most of our discolouration is a result of hyperpigmentation.

Anyway good luck

Hello again, everyone!

Originally Posted by MDC
Thanks Bill for the followup! I’m a couple of days into my second application of wart remover, and would love to try your technique once It’s completed it’s cycle.

No problem! I’d like very much to hear as much feedback as possible, so whether it be observation or opinion, feel free to post!

Originally Posted by ModestoMan
Bill,

Another brilliant post. Thank you. If this works as well as you hope, you will without question win the prize for the most significant transfer of knowledge to Thundersplace in the fewest number of posts .

Have you tried the MSP on your glans? Do you have any special precautions in that regard?

I really appreciate your words, MM. Regarding application to the glans, I have covered it completely in MSP upon each application. In the interests of specificity, I ensure the paste that results from preparing the mixture of water and powder is as thick as possible while still being of low enough viscosity to spread without clumping together. I do not dilute the paste upon application to the glans; the paste that satisfies the above description is applied to shaft, glans and scrotum all the same.

I do not find any stinging or burning below five minutes of application. In fact, I feel little sensation at all, regardless of application time, although by the end of my 10-minute allotment I sometimes feel a “cooling” effect not dissimilar to a mild menthol application. Your question is timely for another reason, though, and I’ll explain further in the main body of my response.

Originally Posted by wherezmyname
First off, I wasn’t exactly sure which product you had used in your experiments. You mention the platinum package, which is the scented variety that is available. But in your original post, you also said that the fragrance was an additional ingredient that you would rather have avoided, so I opted for the blue package.

I’m glad you mentioned this. Unfortunately, the blue variety (Regular Strength) does not use calcium thioglycolate as it’s depilatory but rather barium sulfide, which does not possess the chelating activity we desire (if chelation is indeed the mechanism at work)! To my knowledge, only the platinum and gold-canned products contain calcium thioglycolate, and I have personal experience only with the platinum variety. Just to be certain, you can view it at this link, listed as “Shaving Powder Platinum” under “AVAILABLE PRODUCTS:” http://www.softsheen-carson.com/_us…magicshave.aspx

I know all too well that feeling you described, that excitement of possibility; I have a hunch we PE practitioners come by it more often than normal, given we’re usually forced to figure things out as we go. I wouldn’t have it any other way. Good luck to you! :)

Originally Posted by hobby
I hope someone trying this will use it on only a portion of the shaft and leave some discoloration untreated as a control. Otherwise, results may be hard to determine. Pictures may also help, but changes in lighting, looseness of the skin, whether the skin is flushed with blood or not, etc. Can cause the same degree of hemosiderin staining to appear differently. If you take pics try to keep the conditions as identical as possible.

Several times I thought something might be working only to later discover I had been fooling myself. Hemosiderin stains are most apparent when the shaft skin is palest and most wrinkled (like after swimming in cold water). Anything that irritates the skin can cause it to become, and perhaps remain if the treatments are repeated often enough, slightly redder/pinker from increased blood flow, disguising the stains somewhat.

Using treated and untreated areas for comparison is certainly the best means of ensuring progress. If it hadn’t been for a greedy desire to immediately reap the benefits in total—should any amount—by applying to the entire penis, that certainly would have been a more savvy means of establishing efficacy. Indeed, if anyone will postpone the straightaway gratification of total application to do a treated/untreated comparison, that’d really help out!

For what it’s worth, all of my observations take place in two specific locations: in the center of the shower and, afterwards, in the center of the bathroom. I specify “center” because I’m wary of maintaining as consistent of lighting conditions as possible between screenings. Although illuminated by the same light source, the penis’ coloration takes upon very different hues in the shower. It’s dimly lit in contrast to the open bathroom, sure; but, the drywall paint of the wall and ceiling above me, responsible for the reflection, seem to refract the light in a way that drastically changes the contrasting of close shades. For the purpose of this experiment, then, it’s extremely useful, as it not only shows much more clearly whether or not any color imperfection may exist, but also whether any improvement has been made at all. I always inspect while flaccid, as erections or semi-erections stretch afflicted areas and disperse the coloration over a larger area, lessening the effect.

I’m glad you mentioned pictures as well, although I certainly don’t expect to receive what I myself am unwilling to provide. All the same, it would undoubtedly help!

Originally Posted by avaya1
If, and only if, discolouration is in fact caused by medium depth hemosiderin staining, as opposed to posttraumatic hyperpigmentation of the melasma type (which would also have been treated by the chemical peeling), then what’s to say that just leaving some calcium thioglycolate on the surface of your skin for ten minutes is going to be able to penetrate through to the papillary layer to bind with the relevant metal ions?

The other potential disadvantage of the method is that it can only treat discolouration caused by hemosiderin staining, whereas, to me, at least, it seems far more likely that most of our discolouration is a result of hyperpigmentation.

Anyway good luck

While the aim of this experiment presupposes the root cause of discoloration to be hemosiderin-based, such a claim is still just a theory. Similarly, that thioglycolic acid (or, more specifically, it’s salt form calcium thioglycolate) can sufficiently penetrate first through surface lipids and sebum to reach the epidermis and then onward through it’s four/five layers and epidermal-dermal junction to reach the papillary dermis is, sadly, only a theory. If it were fact, I wouldn’t need waste my time speculating! :)

In all seriousness, the truth is that we simply don’t know if leaving MSP on the the penis for ten minutes will behave as we predict. Besides calcium thioglycolate’s unique penetrating characteristics we also have to consider that the other ingredients may limit, or worse, entirely prevent the TGA from penetrating, if indeed it can. TGA’s chelation profile includes a strong affinity to complex with free iron; still, how that will translate during transdermal application in the presence of many other ingredients is completely unknown.

Post-inflammatory hyperpigmentation (PIH) is indeed a reasonable alternative explanation to PE-induced discoloration. I do, however, disagree with your contention that it is the more likely candidate. PIH is caused under similar circumstances, certainly. But with all the time and attention those of this forum have given to the problem, it would seem likely more would have reported success in their endeavors to rid of discoloration if PIH was the most significant cause. The reason is simple: PIH responds to far more treatments than hemosiderin staining. Consider some of the proposed treatments: arnica, vitamin K, all sorts of various OTC exfoliants ranging from 8-12% glycolic acid to 1-2% salicylic acid, manual scrubbing, extended hot-wraps, “bib-style” wrapping to induce edema, 2-4% hydroquinone, etc. Etc. Ad nauseum. None of the treatments mentioned attained widely-reported success, but two in particular were not only often suggested as possible treatments, but noteworthy for their efficacy in treating PIH: glycolic/salicylic acid and hydroquinone.

At the levels posters reported (8-12% AHA or 1-2% BHA), such acidity wouldn’t even come near that required to reach the papillary dermis. Commercial agencies often report that numerous light chemical peels at the ranges noted prior can equal the effectiveness of a single medium or deep chemical peel; this is patently false. When used in light concentrations, slight, or often unnoticeable desquamination of the stratum corneum occurs, accompanied by either trivial or non-existent sensation. If one were to apply 10% glycolic acid at a pH of 4 (a common formulation) twice a day the aforementioned action would be the only one; the idea that many extremely mild “peels” can, over time, remove the layers of the skin like an onion until finally reaching the papillary dermis misunderstands the process. After a mild peel, the stratum corneum replenishes itself by introducing fresh cells from the stratum lucidum (or whichever layer remains intact). Thus, each light peeling episode removes a new stratum corneum; unfortunately, deeper layers of the epidermis and, more importantly, dermis, remain untouched chemically, progressing as they would without outside input. Simply stated, in order to affect the papillary dermis in terms of “brute force” (exfoliation) one has to reach it. To do so requires at least (commonly) 15% salicylic acid, 70% glycolic acid, 10% TCA or .00001% phenol, each of a decently low pH (OK, all but perhaps the last). :)

How, then, would such light peeling benefit the removal of PIH? Post-inflammatory hyperpigmentation can reside in either the epidermis or dermis; in the prior it takes upon a characteristic brown/tan hue, in the latter a grayish hue. A wood lamp lighting test can determine whether or not the hypermelanin deposition rests in the epidermis or dermis. If located in the dermis, PIH is as similarly intractable as hemosiderin deposition, and treatment would (theoretically) follow the same path. If located in the epidermis, any action that speeds desquamination benefits it’s removal. The stratum spinosum is frequently the site of hyperpigmentation issues in cosmetics, and is the first layer that partakes in keratinization after it’s basal layer “birth.” In the event a light peel removed all of the stratum corneum, the following process would occur: cells would migrate from the stratum lucidum to form a new stratum lucidum; stratum lucidum replaced by cells from stratum granulosum; stratum granulosum replaced by cells from stratum spinosum, and finally stratum spinosum originating from mitosis at the stratum germinativum (basal layer). The implication is clear: as each layer is forced to contribute parts of itself to repair layers above it, over time, layers will replace themselves completely. The epidermis typically rejuvinates itself completely in around 30 days, though this time varies by individual and could be as long as 90 days. This also means that epidermal PIH will typically not remain longer than ~3 months, gelling with most medical evidence. Obvious to all of us enduring long-lasting discoloration, dermal PIH can persist for years, if not indefinitely. Yeah, tell us something new. ;)

What this tells us is this: If the perpetrator is dermal PIH instead of hemosiderin deposition, the distinction is scholastic rather than practical; both birds, same stone. Hydroquinone’s ineffectivity does not necessarily rule out dermal PIH as a possibility due to hydroquinone’s poor dermal permeability and the strength of hydroquinone required to reach the dermis in quantities sufficient to induce hypopigmentation. Medium-strength peels are demonstratively effective, and I *really* hope TGA of some quantity offers a second option. I hope you try it, and I hope it works fabulously!

Ah, the time! It’s terribly early in the morning and I’ve long since passed any sensible length of time to spend on this post, but I will quickly summarize a few thoughts:

1.) Applied the MSP only once since the previous post. Penis state remains about the same; serious improvement from initial application, but improvement has slowed. Could the improvement be a matter of my penis growing more conditioned all the time to the exercises I impose on it, the remaining hemosiderin stains lightening by way of being introduced to no new hemoglobin and giving up minute amounts of hemosiderin by metabolism, or perhaps a slight degree of macrophage activity? It may seem my faith dies quickly, but I’m only looking to stay true to that which I can feel very certain. Wondering harder about secondary ingredients in MSP obfuscating TGA’s permeation. A “pure” TGA solution, either water-based or ethyl-based, would be fantastic!

2.) EDTA. Knowing I’ve seen it thrown around discussions of chelation, specifically in the long ago post highlighting gstlynx’s (spelling?) topical R-ALA application (didn’t he solubilize the ALA in Rogaine?), I searched the forum to find nothing concrete. There are Internet sources selling a powdered calcium EDTA, advertised as a means to detoxify the body of noxious metals by more holistic methods, such as adding the powder to your bath water. Given it’s high water solubility and extremely high affinity for iron (as well as inexpensive price for large quantities), would perhaps a high-concentration EDTA/water bath of, say, 20-30 minutes allow for adequate absorption? Please do not allow my mentioning of another idea convince you I’ve abandoned TGA altogether—that couldn’t be farther from the truth! I’m simply of the philosophy it pays to keep your hands busy while the oven cooks.

I’m feeling very poorly and need to get some rest, so please excuse anything that isn’t appropriately substantiated. I can’t emphasize enough how great it is to have a forum to discuss this, and must thank you all again for your support. Talk to you again soon.

Bill

That’s a very impressive answer. I wonder how well the experiment is currently going for you?

Originally Posted by zarathustra
To do so requires at least (commonly) 15% salicylic acid, 70% glycolic acid, 10% TCA or .00001% phenol, each of a decently low pH (OK, all but perhaps the last). :)

PKa of phenol is indeed 9.95 ;)

Quote
A “pure” TGA solution, either water-based or ethyl-based, would be fantastic!

What do you mean by ethyl-based?

Quote
EDTA. Knowing I’ve seen it thrown around discussions of chelation, specifically in the long ago post highlighting gstlynx’s (spelling?) topical R-ALA application (didn’t he solubilize the ALA in Rogaine?), I searched the forum to find nothing concrete.

From the patent mentioned in your first post:
"The use of formulations containing chelating agents, such as EDTA or desferroxamine (already proposed by some authors, see Meyers in 1966 and Goldman in 1992) give variable, uncertain results, likely due to their difficult diffusion through cutis, since topical way is the most preferred”

Quote
Please do not allow my mentioning of another idea convince you I’ve abandoned TGA altogether—that couldn’t be farther from the truth!

I’m sure no one thinks of that. I will continue the discussion by raising some questions.

1. Mercaptoacetic acid (I really prefer IUPAC names :) ) vs. It’s salt.

First of all, this is highly concerning to me:
Http://www.chemicalbook.com/Product…B6477604_EN.htm

“EC Class:
Toxic; Corrosive

Appearance:
Colorless liquid with a characteristic strong unpleasant odor, lachrymator.

Hazards Identification:
Skin:
May be fatal if absorbed through the skin. Causes skin burns. Strong irritant of the skin.

First Aid Measures:
Skin:
Get medical aid immediately. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.”

This really doesn’t sound like something I’d like to place on my dick.
At least not in “[s]olutions having concentrations comprised in the 0.5-15% w/w range”, as it is claimed in the patent.

Now with the calcium salt it may be different.
However, I still wouldn’t feel comfortable applying things on my skin that contain free thiol groups (the salt is of course made at the carboxylic acidic site: pKa = 3.67, as opposed to the pKa of the thiol group, which is about 10).

2. Potential structure of the compound with the trivalent iron
I assume this would be some kind of octahedral structure, with three anions of mercaptoacetate coordinating the iron cation.
What would be the chemistry of the ligand exchange (thermodynamically and kinetically)?

Edit: why does the automatic correction thingie “correct” my
"Lowercase v-lowercase s-dot-space-lowercase I-lowercase t-lowercase s”
To
“Vs. It’s”
?

This is stupid.

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