Compound: Myrophine
SMILES: O=C(O[C@H]1C=C[C@H]2[C@@H]3N(C)CC[C@@]42[C@H]1Oc5c(OCc6ccccc6)ccc(c45)C3)CCCCCCCCCCCCC
InChIKey: GODGZZGKTZQSAL-VXFFQEMOSA-N
Synonyms: Myrophine, Myrocodine, Myrophinium, Myrophinum, Mirofina, Myristylbenzylmorphine, MYROPHIN, Leucodiniene, Myricodine, Myrocodin, 467-18-5, Myrophine [INN:BAN:DCF], 3-benzylmorphine 6-myristate, myristyl benzylmorphine, benzylmorphinyl myristate, DEA No. 9308, Mirofina [INN-Spanish], Myrophinum [INN-Latin], 3-benzyloxy-6-myristoyloxymorphine, UNII-417TUP54OL, 417TUP54OL, IDS-NM-013, Morphine, O3-benzyl ether, 6-myristate, benzylmorphine myristic acid ester, 3-O-Benzyl-6-O-myristoylmorphin, NIH 5986 A, MYROPHINE [INN], MYROPHINE [MI], 3-Benzyloxy-N-methyl-6-myristoyloxy-4,5-epoxymorphin-7-en, CHEBI:59860, DTXSID40196911, Mirofina (INN-Spanish), Myrophinum (INN-Latin), 3-Benzyloxy-4,5alpha-epoxy-17-methyl-17-morphinen-6-ylmyristat, 3-benzyloxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-yl myristate, 3-benzyloxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-yl tetradecanoate, Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, tetradecanoate (ester), Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, 6-tetradecanoate, (5.alpha.,6.alpha.)-, RefChem:160457, DTXCID80119402, MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(PHENYLMETHOXY)-, 6-TETRADECANOATE, (5ALPHA,6ALPHA)-, GODGZZGKTZQSAL-UHFFFAOYSA-N, SCHEMBL26043, CHEMBL4297082, SCHEMBL29851007, NS00067973, 3-(Benzyloxy)-17-methyl-5alpha-7,8-didehydro-4,5-epoxymorphinan-6alpha-yl tetradecanoate, Myrophine; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, 6-tetradecanoate, (5a,6a)-; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, tetradecanoate (ester), (5a,6a)- (9CI); Morphine, O3-benzyl ether, 6-myristate (6CI); L
Theoretical properties:
molecular_formula: C38H51NO4
molecular_weight: 585.8 g/mol
exact_mass: 585.38180911 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 17
heavy_atom_count: 43
topological_polar_surface_area: 48 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Myrophine is the 3-O-benzyl and 6-myristyl derivative of morphine, for which it is a prodrug. Myrophine is almost invariably used as the hydrochloride. It has a role as an opioid analgesic and a prodrug. It is a benzyl ether and a tetradecanoate ester. It is functionally related to a morphine.
chebi: The 3-<em>O</em>-benzyl and 6-myristyl derivative of morphine, for which it is a prodrug. Myrophine is almost invariably used as the hydrochloride.
chembl: MYROPHINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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 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 US, 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.