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Ambrein

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Ambrein
Names
IUPAC name (1R,2R,8aS)-1--4-methylhex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Other names Ambrein
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.784 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1Key: BIADSXOKHZFLSN-CQDHYIGWSA-N
  • InChI=1/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1Key: BIADSXOKHZFLSN-CQDHYIGWBE
SMILES
  • C/C(=C\CC12(CCCC(C2CC1(C)O)(C)C)C)/CC3C(=C)CCCC3(C)C
  • O1(CCC3(1CC\C=C(/C)CC2C(=C)\CCCC2(C)C)(C)CCCC3(C)C)C
Properties
Chemical formula C30H52O
Molar mass 428.745 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Ambrein is a fragrant substance that is used in the perfume industry. It is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris.

It is a triterpene alcohol.

It has been shown to act as an analgesic and increase sexual behaviour in rats, providing some support for its traditional aphrodisiac use.

References

  1. Sandroni P. Aphrodisiacs past and present: a historical review. Clinical Autonomic Research. 2001 Oct;11(5):303-7. doi:10.1007/BF02332975 PMID 11758796
  2. Taha SA. Studies on the mode of action of ambrein as a new antinociceptive compound. Japanese Journal of Pharmacology. 1992 Oct;60(2):67-71. PMID 1479744
  3. Taha SA, Islam MW, Ageel AM. Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats. Archives Internationales de Pharmacodynamie et de Therapie. 1995 Mar-Apr;329(2):283-94. PMID 8540767


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