Androstadienone

{{Short description|Chemical compound}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 438860644

| IUPAC_name = (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

| image = Androstadienone chemical structure.png

| width = 200px

| image2 = Androstadienone-based-on-xtal-3D-bs-17.png

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 4075-07-4

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = ZUZ4FHD36E

| ATC_prefix = none

| PubChem = 92979

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 83932

| C=19 | H=26 | O=1

| smiles = C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HNDHDMOSWUAEAW-VMXHOPILSA-N

}}

Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class endogenous steroid that has been described as having potent pheromone-like activities in humans.{{cite journal | vauthors = Wyart C, Webster WW, Chen JH, Wilson SR, McClary A, Khan RM, Sobel N | title = Smelling a single component of male sweat alters levels of cortisol in women | journal = The Journal of Neuroscience | volume = 27 | issue = 6 | pages = 1261–1265 | date = February 2007 | pmid = 17287500 | pmc = 6673596 | doi = 10.1523/JNEUROSCI.4430-06.2007 | doi-access = free }} The compound is synthesized from androstadienol by 3β-hydroxysteroid dehydrogenase, and can be converted into androstenone (a more potent and odorous pheromone) by 5α-reductase, which can subsequently be converted into 3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase.{{cite thesis |title=Biochemical pathways in human testicular steroidogenesis| vauthors = Weusten AM | degree = Ph.D. |year=1989 |publisher=Pressa Trajectina, Universiteit Utrecht |url= http://repository.ubn.ru.nl/bitstream/handle/2066/113615/mmubn000001_074818627.pdf?sequence=-1}}

Androstadienone is related to the androgen sex hormones; however, androstadienone does not exhibit any androgenic or anabolic effects. Though it has been reported to significantly affect the mood of heterosexual women and homosexual men, it does not alter behavior overtly,{{cite journal | vauthors = Lundström JN, Olsson MJ | title = Subthreshold amounts of social odorant affect mood, but not behavior, in heterosexual women when tested by a male, but not a female, experimenter | journal = Biological Psychology | volume = 70 | issue = 3 | pages = 197–204 | date = December 2005 | pmid = 16242537 | doi = 10.1016/j.biopsycho.2005.01.008 | s2cid = 12401158 }}{{cite web | vauthors = Gabrielsen P |url=http://www.huffingtonpost.com/2013/06/01/mens-sweat-pheromone-cooperation_n_3371709.html |title={{as written|Mens' [sic]}} Sweat Pheromone, Androstadienone, Influences Cooperation In Other Men |website=HuffPost |date=2 June 2013 |access-date=March 14, 2016}}{{cite web|url=http://houseofpheromones.com/human-pheromone-effects-molecules/ |title=Human Pheromone Molecules | work = House of Pheromones |access-date=March 14, 2016 |archive-url=https://web.archive.org/web/20160327022519/http://houseofpheromones.com/human-pheromone-effects-molecules/ |archive-date=March 27, 2016 |url-status=dead }}{{cite web | vauthors = Yuhas D | date = 1 May 2014 |url= http://www.scientificamerican.com/article/human-sexual-responses-boosted-by-bodily-scents/ |title=Human Sexual Responses Boosted by Bodily Scents |website=Scientific American |access-date=March 14, 2016}} although it may have more subtle effects on attention.{{cite journal | vauthors = Hummer TA, McClintock MK | title = Putative human pheromone androstadienone attunes the mind specifically to emotional information | journal = Hormones and Behavior | volume = 55 | issue = 4 | pages = 548–559 | date = April 2009 | pmid = 19470369 | doi = 10.1016/j.yhbeh.2009.01.002 | s2cid = 17022112 }}

Androstadienone is commonly sold in male fragrances; it is purported to increase sexual attraction. Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in female subjects.{{cite journal | vauthors = Grosser BI, Monti-Bloch L, Jennings-White C, Berliner DL | title = Behavioral and electrophysiological effects of androstadienone, a human pheromone | journal = Psychoneuroendocrinology | volume = 25 | issue = 3 | pages = 289–299 | date = April 2000 | pmid = 10737699 | doi = 10.1016/s0306-4530(99)00056-6 | s2cid = 41960611 }}