Phenomorphan

Phenomorphan
	File:Phenomorphan.svg
	File:Phenomorphan 3D BS.png
Clinical data
Other names	(-)-3-hydroxy- N- (2-phenylethyl) morphinan
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name 17-(2-Phenylethyl)morphinan-3-ol;
CAS Number	468-07-5 check;
PubChem CID	5362458;
ChemSpider	16735962 check;
UNII	26HXE4B73P;
KEGG	D12688 check;
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C24H29NO
Molar mass	347.502 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@H]12)c4c3)CCc5ccccc5;
	InChI InChI=1S/C24H29NO/c26-20-10-9-19-16-23-21-8-4-5-12-24(21,22(19)17-20)13-15-25(23)14-11-18-6-2-1-3-7-18/h1-3,6-7,9-10,17,21,23,26H,4-5,8,11-16H2/t21-,23+,24+/m0/s1 check; Key:CFBQYWXPZVQQTN-QPTUXGOLSA-N check;
	(verify)

Phenomorphan^[2] is an opioid analgesic. It is not currently used in medicine, but has similar side-effects to other opiates, which include itching, nausea and respiratory depression.

Phenomorphan is a highly potent drug due to the N-phenethyl group, which boosts affinity to the μ-opioid receptor, and so phenomorphan is around 10x more potent than levorphanol, which is itself 6-8x the potency of morphine. Other analogues where the N-(2-phenylethyl) group has been replaced by other aromatic rings^[3] are even more potent, with the N-(2-(2-furyl)ethyl) and the N-(2-(2-thienyl)ethyl) analogues being 60x and 45x stronger than levorphanol, respectively.^[4]

References

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[1] Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[2] US patent 2885401, Grussner A, Hellerbach J, Schnider O, "Process for making morphinan derivatives and products available thereby", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[3] US patent 2970147, Andre Grussner, Joseph Hellerbach, Otto Schnider, "3-hydroxy-N-(heterocyclic-ethyl)-morphinans", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[4] Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

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Phenomorphan

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Phenomorphan

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