3-Monoacetylmorphine
Chemical compound
- none
- AU: S9 (Prohibited substance)
- UK: Class A
- US: Schedule I
- 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
- 5140-28-3
Y
- 5462504
- 4575431
Y
- 9N7243EY5T
- DTXSID30183774
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- CC(=O)OC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)C=C1
InChI
- InChI=1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1
Y
- Key:GMLREHXYJDLZOU-LEPYJNQMSA-N
Y
3-Monoacetylmorphine (3-MAM) or 3-acetylmorphine is a less active metabolite of heroin (diacetylmorphine), the other two being morphine and more active 6-monoacetylmorphine (6-MAM).
Because of the acetyl-group in 3-position, 3-MAM has relatively weak affinity to μ-opioid receptors.
As 3-O-acetylmorphine-6-O-sulfate (C19H23NO7S), where 6-OH is changed to 6-O-SO3, it can act as a potent, centrally acting morphine derivative and has important analgesic properties.[1][2][3]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/a/ab/3-MAM-6-Sulphur.svg/150px-3-MAM-6-Sulphur.svg.png)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Acetyl_groups_of_heroin.svg/150px-Acetyl_groups_of_heroin.svg.png)
References
- ^ Houdi AA, Kottayil S, Crooks PA, Butterfield DA (March 1996). "3-O-acetylmorphine-6-O-sulfate: a potent, centrally acting morphine derivative". Pharmacology, Biochemistry, and Behavior. 53 (3): 665–671. doi:10.1016/0091-3057(95)02067-5. PMID 8866970. S2CID 14870642.
- ^ Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA (August 2006). "Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners". Bioorganic & Medicinal Chemistry Letters. 16 (16): 4291–4295. doi:10.1016/j.bmcl.2006.05.060. PMID 16777416.
- ^ Brock CP, Kottayil S, Butterfield DA, Crooks PA (January 1996). "A Dihydromorphine-6-O-sulfate". Acta Crystallographica Section C. 52 (1): 122–5. doi:10.1107/S0108270195010250.
- v
- t
- e
(MOR)
(DOR)
(KOR)
(NOP)
Agonists |
|
---|---|
Antagonists |
|
- Enkephalinase inhibitors: Amastatin
- BL-2401
- Candoxatril
- D -Phenylalanine
- Dexecadotril (retorphan)
- Ecadotril (sinorphan)
- Kelatorphan
- Racecadotril (acetorphan)
- RB-101
- RB-120
- RB-3007
- Opiorphan
- Selank
- Semax
- Spinorphin
- Thiorphan
- Tynorphin
- Ubenimex (bestatin)
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)