Androstenol

Androstenol
Clinical data
ATC code	none;
Identifiers
	IUPAC name (2R,5R,7S,15R)-2,15-Dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-ol;
CAS Number	1153-51-1 ;
PubChem CID	101989;
IUPHAR/BPS	2761;
DrugBank	DB01889 ;
ChemSpider	92136 ;
UNII	48K9VAM062;
ChEBI	CHEBI:40933 ;
ChEMBL	ChEMBL142348 ;
CompTox Dashboard (EPA)	DTXSID2075394 ;
ECHA InfoCard	100.013.248
Chemical and physical data
Formula	C19H30O
Molar mass	274.448 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:KRVXMNNRSSQZJP-PHFHYRSDSA-N ;
	(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]

^ 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.
^ 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.
^ Kunzig R (November 2000). "The Biology of Truffles". Discover Magazine.
^ 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.

[Kaminski2006-1] 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.

[SemwalKumar2013-2] 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.

[Pause2004-4] 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.

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Clinical data

ATC code	none
Identifiers
IUPAC name (2R,5R,7S,15R)-2,15-Dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadec-13-en-5-ol
CAS Number	1153-51-1^Y
PubChem CID	101989
IUPHAR/BPS	2761
DrugBank	DB01889^Y
ChemSpider	92136^Y
UNII	48K9VAM062
ChEBI	CHEBI:40933^Y
ChEMBL	ChEMBL142348^Y
CompTox Dashboard (EPA)	DTXSID2075394
ECHA InfoCard	100.013.248
Chemical and physical data
Formula	C₁₉H₃₀O
Molar mass	274.448 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:KRVXMNNRSSQZJP-PHFHYRSDSA-N^Y
^NY (what is this?) (verify)