Myrophine

Myrophine

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Systematic (IUPAC) name
7,8-didehydro-4,5α-epoxy-17-methyl-3-(phenylmethoxy)-morphinan-6-ol tetradecanoate
Clinical data
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
CAS Number	467-18-5
ATC code	none
PubChem	CID: 5362457
ChemSpider	4515045
UNII	417TUP54OL Y
ChEBI	CHEBI:59860 Y
Synonyms	Myristylbenzylmorphine
Chemical data
Formula	C38H51NO4
Molecular mass	585.82 g/mol
SMILES CCCCCCCCCCCCCC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OCC6=CC=CC=C6)CCN3C
InChI InChI=1S/C38H51NO4/c1-3-4-5-6-7-8-9-10-11-12-16-19-34(40)42-33-23-21-30-31-26-29-20-22-32(41-27-28-17-14-13-15-18-28)36-35(29)38(30,37(33)43-36)24-25-39(31)2/h13-15,17-18,20-23,30-31,33,37H,3-12,16,19,24-27H2,1-2H3/t30-,31+,33-,37-,38-/m0/s1 Key:GODGZZGKTZQSAL-VXFFQEMOSA-N
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Myrophine (Myristylbenzylmorphine) is an opiate analogue that was developed in 1952. It is a derivative of morphine.

Myrophine is substituted with a 3-benzyl group and a 6-myristyl chain. It is metabolised to form benzylmorphine and then further to morphine, and so is a long-acting prodrug for morphine, but with a slow onset of effects. It is weaker than morphine as an analgesic but longer lasting in effects, and was thought to have more local anesthetic effect than morphine, though with a somewhat greater tendency to cause histamine reactions like itching and rash. In addiction studies conducted in human subjects in the 1950s, myrophine did not substitute for morphine in withdrawal, did not produce notable morphine-like effects, and did not produce addiction or dependence regardless of dose or how it was administered. Consequently it was thought to be useful in treating pain in addicts who were being detoxified from other opioid drugs.

It is a Schedule I drug in the USA, considered to have high potential for abuse and no medical applications, and is controlled under international drug conventions. Myrophine is almost invariably used as the hydrochloride (free base conversion ratio 0.94) and has a DEA Administrative Controlled Substance Control Number of 9308. Myrophine is a Class A controlled substance in the UK, and is on the UN's Yellow list.