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Androstenol

Androstenol
Clinical data
ATC code
  • none
Identifiers
  • (2R,5R,7S,15R)-2,15-Dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.013.248 Edit this at Wikidata
Chemical and physical data
FormulaC19H30O
Molar mass274.448 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CC[C@H](C4)O)C
  • InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1 checkY
  • Key:KRVXMNNRSSQZJP-PHFHYRSDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Androstenol, also known as 5α-androst-16-en-3α-ol (shortened to 3α,5α-androstenol or 3α-androstenol), is a 16-androstene class steroidal pheromone and neurosteroid in humans and other mammals, notably pigs.[1] It possesses a characteristic musk-like odor.[2]

Androstenol, or a derivative, is found in black truffles. This was offered as an explanation for how pigs locate them deep in the ground: Androstenol is produced in the saliva of male pigs. However, experiments in France using pigs to scent truffles, truffle scent extract, and purified androstenol showed that pigs responded to the first two (actually trying to eat dirt containing the truffle extract), but ignored the androstenol.[3]

A stereoisomer of androstenol, 3β-androstenol (5α-androst-16-en-3β-ol), is also endogenous to humans (as well as to pigs), behaving as a pheromone and contributing to axillary odor.[4]

Biosynthesis

In humans and boars, androstenol is biosynthesized in the testes.[1] Pregnenolone is metabolized into androstadienol by the 16-ene-synthetase activity of CYP17A1.[1] Androstadienol is then sequentially converted into androstenol by 3β-hydroxysteroid dehydrogenase (androstadienol to androstadienone), 5α-reductase (androstadienone to androstenone), and 3α-hydroxysteroid dehydrogenase (androstenone to androstenol), in a manner analogous to the biosynthesis of 3α-androstanediol from dehydroepiandrosterone (DHEA).[1][5] Androstenol may also be synthesized in the adrenal glands and the ovaries in humans.[1] In addition, androstenol may be synthesized in the human nasal mucosa from androstenone, and likely also from androstadienol and androstadienone in this area.[1]

Distribution

Considerable amounts of androstenol are present in human urine, and it is also present in the blood plasma and saliva of humans and pigs as well as in the axillary sweat of humans.[1] Due to its ability to cross the blood–brain barrier, androstenol is likely present in the central nervous system as well.[1]

Biological activity

Androstenol, similarly to the related endogenous steroids 3α-androstanediol and androsterone, has been found to act as a potent positive allosteric modulator of the GABAA.[1] It has been proposed that this action may mediate the pheromone effects of androstenol.[1] Moreover, as androstadienol, androstadienone, and androstenone are all converted into androstenol, it could mediate their pheromone effects as well.[1] In animals, androstenol has been found to produce anxiolytic-like, antidepressant-like, and anticonvulsant effects.[1] Androstenol has also been found to modify the behavioral and social responses of humans.[1] In addition, androstenol has been found to decrease luteinizing hormone (LH) pulse frequency during the follicular phase of the human menstrual cycle.[6] In accordance, it has been proposed that androstenol may be involved in the menstrual synchrony of women.[2][6]

In contrast to androstenol (3α-androstenol), its 3β-epimer, 3β-androstenol, does not potentiate the GABAA receptor, even at high concentrations.[1] This is in accordance with other 3β-hydroxy steroids, including isopregnanolone, epipregnanolone, 3β-dihydroprogesterone, and 3β-androstanediol, which similarly do not act as such, in contrast to their 3α-hydroxy variants.[1]

Androstenol, along with several isomers of androstanol, is an antagonist of the constitutive androstane receptor (CAR).[7] Androstenol has minimal or no androgenic activity.[2]

See also

References

  1. ^ a b c d e f g h i j k l m n o Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA (May 2006). "The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors". The Journal of Pharmacology and Experimental Therapeutics. 317 (2): 694–703. doi:10.1124/jpet.105.098319. PMID 16415088. S2CID 95393004.
  2. ^ a b c Semwal A, Kumar R, Teotia UV, Singh R (2013). "Pheromones and their role as aphrodisiacs: A review". Journal of Acute Disease. 2 (4): 253–261. doi:10.1016/S2221-6189(13)60140-7.
  3. ^ Kunzig R (November 2000). "The Biology of Truffles". Discover Magazine.
  4. ^ Pause BM (October 2004). "Are androgen steroids acting as pheromones in humans?". Physiology & Behavior. 83 (1): 21–9. doi:10.1016/S0031-9384(04)00345-2. PMID 15501487.
  5. ^ Johannes J, Weusten AM (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.
  6. ^ a b Henderson LP (June 2007). "Steroid modulation of GABAA receptor-mediated transmission in the hypothalamus: effects on reproductive function". Neuropharmacology. 52 (7): 1439–53. doi:10.1016/j.neuropharm.2007.01.022. PMC 1985867. PMID 17433821.
  7. ^ Meanwell NA (8 December 2014). Tactics in Contemporary Drug Design. Springer. pp. 182–. ISBN 978-3-642-55041-6.
Quelle: https://en.wikipedia.org/wiki/Androstenol