Ambrein

Ambrein
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
CAS Number	473-03-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:78306 ;
ChemSpider	10000763 ;
ECHA InfoCard	100.006.784
PubChem CID	11826112;
CompTox Dashboard (EPA)	DTXSID00883390 ;
	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/s1 Key: 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/s1 Key: BIADSXOKHZFLSN-CQDHYIGWBE;
	SMILES C/C(=C\CC[C@@H]1[C@]2(CCCC(C2CC[C@@]1(C)O)(C)C)C)/CC[C@@H]3C(=C)CCCC3(C)C; O[C@@]1(CCC3[C@]([C@H]1CC\C=C(/C)CC[C@@H]2C(=C)\CCCC2(C)C)(C)CCCC3(C)C)C;
Properties
Chemical formula	C30H52O
Molar mass	428.745 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 it has been proven to increase sexual behavior in rats,^[3] providing some support for its traditional aphrodisiac use.

References

^ Sandroni, P (Oct 2001). "Aphrodisiacs past and present: a historical review". Clinical Autonomic Research. 11 (5): 303–7. doi:10.1007/BF02332975. PMID 11758796.
^ 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.
^ 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 Thérapie. 329 (2): 283–94. PMID 8540767.

This biochemistry article is a stub. You can help Wikipedia by expanding it.

[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 Thérapie. 329 (2): 283–94. PMID 8540767.

[1]

[2]

[3]