Ambrein

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Ambrein
Ambrein.svg
Names
IUPAC name
(1R,2R,8aS)-1-[(E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Other names
Ambrein
Identifiers
473-03-0 YesY
ChEBI CHEBI:78306 YesY
ChemSpider 10000763 YesY
Jmol-3D images Image
Image
PubChem 11826112
Properties
C30H52O
Molar mass 428.73 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Ambrein is a triterpene alcohol that 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.[1] Although ambrein itself is odorless, it serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other oderants.

It has been shown to act as an analgesic[2] and increase sexual behaviour in rats,[3] providing some support for its traditional aphrodisiac use.

References[edit]

  1. ^ Sandroni, P (Oct 2001). "Aphrodisiacs past and present: a historical review". Clinical Autonomic Research 11 (5): 303–7. doi:10.1007/BF02332975. PMID 11758796. 
  2. ^ Taha, SA (Oct 1992). "Studies on the mode of action of ambrein as a new antinociceptive compound". Japanese Journal of Pharmacology 60 (2): 67–71. doi:10.1254/jjp.60.67. PMID 1479744. 
  3. ^ Taha, SA; Islam, MW; Ageel, AM (1995). "Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats". Archives Internationales de Pharmacodynamie et de Therapie 329 (2): 283–94. PMID 8540767.