Ambrein

Ambrein
Names
	IUPAC name (1R,2R,4aS,8aS)-1-{(3E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-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;
UNII	1N9JB373FJ ;
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. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.

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

Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It reduces these contractions by serving as an antagonist and interfering with Ca²⁺ ions from outside the cell.