DHEA Metabolites explained
What is the difference between DHEA 1-DHEA 4-DHEA Androsterone and 7-Keto?
 DHEA (dehydroepiandrosterone)
Main effects
+ Anti-aging (youthful energy)
+ Exercise endurance
+ Recovery
+ Fat loss
+ Muscle sparing (anti-catabolic)
+ Immune system
 Primary metabolite –
5-androstenediol (5-AD)
Description –
DHEA is considered "generic" or regular DHEA. It can technically be called 5-DHEA, since the double bond is located in the 5th position.
DHEA has been popular in the life extension crowd since the 1980’s. It's typically used for its ability to support energy and general wellbeing at a dose of 50-100mg/day. (1-3) More recently, higher doses of DHEA have been used to improve body composition due to DHEA’s mild anabolic and thermogenic effects. (1, 4) This makes DHEA an excellent choice for cutting during a calorie deficient diet, since DHEA has good muscle sparing properties. (1, 17)
DHEA converts to testosterone at a rate of about 1%, however it has high conversion to 5-androstenediol, where it gets its mild androgenic and anabolic effects. (5-8) DHEA’s thermogenic properties come from its conversion to 7-oxo-DHEA. (4)
Due to DHEA’s mild androgenic effects it rarely produces hair loss or acne. Although DHEA has moderate estrogenic effects, it rarely produces gyno or undesirable estrogenic side effects.(1-3) Some more sedentary users have reported anxiety or sleeplessness with DHEA, which is likely related to the neurosteroid activity in the brain. (3) However, this effect is also reported as “motivational energy” which is a frequently reported benefit of DHEA.
Because of DHEA’s wide range of benefits and its balanced hormonal properties it can easily be used for cutting, or to keep gains lean during a lean mass building cycle.
|
 4-DHEA (4-dehydroepiandrosterone)
Main effects –
+ Muscle mass (nitrogen retention)
+ Strength
+ Blood volume (hematopoietic)
+ Recovery
+ IGF-1 & GH
 Primary metabolite –
4-androstenediol (4-AD)
Description –
4-DHEA is a naturally occurring DHEA isomer. It’s structure closely resembles regular DHEA but the double bond in the 4th position dramatically changes its effects.
4-DHEA readily converts to 4-androstenediol, rather than 5-androstenediol, boosting its anabolic potency more than 2x over regular DHEA. (6-8, 11) 4-DHEA is also expected to have a higher conversion rate to testosterone compared to regular DHEA. (6, 7) The 4-DHEA also lacks the calorie burning thermogenic properties, therefore offering superior calorie retention for a bulking effect. (4) This increased anabolic potency and reduced thermogenic action will lead to noticeable gains in strength, lean tissue growth, and weight gain.
4-DHEA will have mild estrogen conversion that can be easily balanced with a non-aromatizing steroid like androsterone or 1-DHEA. Overall gains will be similar to the original “4-AD” banned in the 2004 Steroid Control Act.
As with the other DHEA isomers, 4-DHEA is naturally occurring and non-toxic. (9) Side-effects such as oily skin or reduced fertility are considered mild and temporary. The most notable side-effect would be suppression of natural testosterone production, which makes PCT necessary after a cycle. Overall 4-DHEA is a very safe and effective lean muscle building agent.
The only downfall to 4-DHEA is its high cost due to the high dose that is required to see significant muscle building effects.
|
| †:The “Super” (ex., "Super-5-DHEA") signifies a fatty ester attachment to the steroid molecule to assist in bioavailability. | |
 1-DHEA (1-dehydroepiandrosterone)
Main effects –
+ Muscle mass (nitrogen retention)
+ Strength
+ Hardening
+ Bloat reduction
+ Recovery
 Primary metabolite –
1-androstenediol (1-AD)
Description –
1-DHEA is a naturally occurring DHEA isomer which cannot convert to testosterone or estrogen — but instead converts to the non-estrogenic 1-testosterone. (10)
The total conversion to 1-testosterone is probably less than 2%. (6,7) However, 1-DHEA gets most of its effects from conversion to 1-androstenediol, which has potent muscle building and hardening effects in and of itself. (8, 11, 12) 1-androstenediol was sold as “1-AD” prior to the 2004 Steroid Control Act, and was known for producing rapid gains in lean mass with zero water retention or bloat.
1-DHEA does not convert to estrogen nor does it activate the estrogen receptor like DHEA is known to do. (13) It could be referred to as “dry DHEA”. Because of this, it will stack well with other estrogenic steroids such as 4-DHEA to produce† clean gains in muscle tissue.
As with the other DHEA isomers, 1-DHEA is naturally occurring and non-toxic. (14) Side-effects such as oily skin, reduced fertility or increased hair shedding are considered mild and temporary. The most notable side-effect would be suppression of natural testosterone production, which makes PCT necessary after a cycle. This makes 1-DHEA a very safe, legal and effective lean muscle building agent. Some users have reported lethargy with 1-DHEA. This seems to be less severe when balanced with DHEA or 4-DHEA which tend to have an anti-lethargic effect.
|
 7-oxo-DHEA (AKA 7-Keto DHEA) (7-oxo-dehydroepiandrosterone)
Main effects –
+ Fat loss
+ Weight loss
+ Muscle sparing (anti-catabolic)
+ Immune supporting
 Primary metabolite –
Androstenetriol (AET)
Description –
7-oxo-DHEA is a naturally occurring metabolite of DHEA. It’s well known for its weight loss effect due to its strong thermogenic action. (4, 15, 16)
The strong thermogenic effect from 7-oxo-DHEA come from its ability to increase two thermogenic enzymes, which increases the body’s ability to burn off calories as heat. (4) Although DHEA shares a similar effect, 7-oxo-DHEA is about 2.5x more active than DHEA. (4) Human studies have shown that 7-oxo-DHEA can increase weight loss, with a majority of weight loss being actual fat tissue. (15-16) Aside from the thermogenic action, 7-oxo-DHEA also appears to be an aromatase inhibitor, which can reduce estrogen levels.
Because of the modification in the 7th position, 7-oxo-DHEA cannot convert to testosterone or estrogen, nor does it have any androgenic or anabolic effects. (15) Because of this, it does not produce side-effects such as hair loss, acne or prostate inflammation. It also blocks the catabolic effect of cortisol, which helps to retain muscle during a low calorie diet.
Side-effects of 7-oxo-DHEA may include anxiety or sleeplessness similar to regular DHEA due to the neuro-stimulating effect. However, this is generally mild, and seems to only occur in some users. Overall 7-oxo-DHEA is very tolerable and safe at the typical 100-200mg/day dose. (15, 16)
While 7-oxo-DHEA can be useful for a cutting or weight loss protocol, it would not be wise to use during a bulking or mass building cycle. Its tendency to increase the metabolism and rate of calorie burning will make it difficult to build additional muscle mass. (4)
|
|
|
|
 R-DHEA (androsterone)
Main effects –
+ Strength
+ Hardening
+ Bloat reduction
+ Recovery
+ Anti-estrogen
+ Sex drive
+ Aggression
 Primary metabolite –
Androstanediol (5-AA)
Description –
R-DHEA is known as “Reduced DHEA” because it is a 5a-reduced metabolite of DHEA. It’s more commonly referred to as androsterone.
This naturally occurring hormone cannot convert to testosterone, but instead converts to the dihydrotestosterone (DHT). (10, 18) Similar to testosterone, DHT is responsible for masculine traits such as aggression, sex drive, and physical strength. (19,20) However, because DHT cannot convert to estrogen, it also helps reduce fat storage and water retention, making it an excellent steroid for increasing muscular hardness and vascularity.
R-DHEA will stack well with 5-DHEA or 4-DHEA as it will help reduce water retention from under the skin, thus creating a “dry” and hard appearance. R-DHEA also has moderate anabolic properties thus allowing it to help enhance lean muscle gains. (21)
Strength gains will also be noticeable with R-DHEA due to its strong androgenic effect which will activate the central nervous system and increase muscular power. (20) This will increase explosive power with minimal bodyweight increase. The increased aggression is typically a welcomed benefit, which manifests as increased confidence and an “alpha male” feeling in sexual and social activities.
The strong androgenic action from R-DHEA will also help support libido and erection hardness. (20) This makes R-DHEA useful to help counter the sexually suppressive effects from other steroids. The powerful androgenic effect will also block estrogenic effects, and help prevent (and reverse) gyno. (22, 23)
Side-effects from R-DHEA will be limited to androgenic side-effects such as oily skin, acne, and increased hair shedding if the user is prone. These side effects are mild and temporary for most users.
|
|
|
|
|
|
References –
1. DHEA treatment for HIV patients: Effects on mood, androgenic and anabolic parameters.
Rabkin, J., et al.
Psychoneuro endocrinology. R. 25, 53-68. 2000
2. Activation of immune function by dehydroepiandrosterone (DHEA) in age- advanced men.
Khorram O, et al.
J Gerontol 1997; 52A:M1- M7.
3. Effects of replacement dose of dehydroepiandrosterone in men and women of advancing age.
Morales AJ, et al
J Clin Endocrinol Metab. 1994 Jun;78(6):1360-7. Erratum in: J Clin Endocrinol Metab 1995 Sep;80(9):2799.
4. Ergosteroids: induction of thermogenic enzymes in liver of rats treated with steroids derived from dehydroepiandrosterone.
LARDY H, et al.
Proc Natl Acad Sci USA 92: 6617-6619, 1995.
5. Dehydroepiandrosterone: kinetics of metabolism in normal men and women.
Bird CE et al.
J Clin Endocrinol Metab. 1978 Oct;47(4):818-22.
6. In vivo conversion of dehydroisoandrosterone to plasma androstenedione and testosterone in man.
Horton R, et al.
J Clin Endocrinol Metab. 1967 Jan;27(1):79-88.
7. In vitro metabolism of androgens in whole human blood.
Blaquier et al.
Acta Endocrinol (Copenh). 1967 Aug;55(4):697-704. No abstract available.
8. Androgens and anabolic agents
Julius A. Vida
Chemistry and pharmacology (1969)
9. METABOLISM OF ANDROST-4-ENE-3,17-DIONE-4-14C BY RABBIT SKELETAL MUSCLE SUPERNATANT FRACTION. ISOLATION OF 3BETA-HYDROXYANDROST-4-EN-17-ONE-14C AND TESTOSTERONE-14C.
THOMAS et al.
J Biol Chem. 1964 Mar;239:766-72
10. Seized designer supplement named “1-Androsterone” identification as 3b-hydroxy-5a-androst-1-en-17-one and its urinary elimination.
Maria K et al.,
Steroids. 2011 Feb 16.
11. Circulating bioactive androgens in midlife women.
Chen et al.
J Clin Endocrinol Metab. 2006 Nov;91(11):4387-94. Epub 2006 Aug 29.
12. Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
Chen Fet al.
J Steroid Biochem Mol Biol. 2004 Aug;91(4-5):247-57.
13. Direct agonist/antagonist functions of dehydroepiandrosterone.
Chen et al.
Endocrinology. 2005 Nov; 146(11):4568-76. Epub 2005 Jun 30
14. Testosterone metabolism revisited: discovery of new metabolites.
Pozo, et al.
Anal Bioanal Chem. 2010 Oct;398(4):1759-70.
15. A randomized, double blind, placebo controlled study of 3 – acetyl – 7 – oxo – dehydroepiandrosterone in healthy overweight adults.
Kalman, D., et al.
(2000). Curr. Ther. Res. 61, 435-442.
16. The effect of 7 – keto Naturalean on weight loss: A randomized, double blind placebo controlled trial. Zenk, J., et al.
(2002). Curr. Ther. Res. 63, 263-272.
17. Antiglucocorticoid function of androstenetriol. Psychoneuroendocrinology
Loria RM. Et al.
1997;22 Suppl 1:S103-8.
18. Physiological Changes in Dehydroepiandrosterone Are Not Reflected by Serum Levels of Active Androgens and Estrogens But of Their Metabolites: Intracrinology
Fernand Labrie, et al.
J Clin Endocrinol Metab. 1997 Aug;82(8):2403-9
19. Evaluation of androgen antagonism of estrogen effect by dihydrotestosterone.
Hung TT, et al.
J Steroid Biochem. 1983 Oct;19(4):1513-20.
20. The effects of transdermal dihydrotestosterone in the aging male: a prospective, randomized, double blind study.
Kunelius P, et al.
J Clin Endocrinol Metab. 2002 Apr;87(4):1467-72.
21. Comparative activities of compounds of the androsterone-testosterone series.
Deanesly R, et al.
Biochem J. 1936 Feb;30(2):291-303.
22. Treatment of persistent pubertal gynecomastia with dihydrotestosterone heptanoate.
Eberle AJ, et al
J Pediatr. 1986 Jul;109(1):144-9.
23. Successful percutaneous dihydrotestosterone treatment of gynecomastia occurring during highly active antiretroviral therapy: four cases and a review of the literature.
Benveniste O et al.
Clin Infect Dis. 2001 Sep 15;33(6):891-3.
|
|
