3-Monoacetylmorphine
3-Monoacetylmorphine
![Structural formula](../I/m/3-MAM.svg.png) |
![Ball-and-stick model](../I/m/3-Monoacetylmorphine_molecule_ball.png) |
Clinical data |
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Routes of administration |
Intravenous |
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ATC code |
none |
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Legal status |
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Legal status |
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Identifiers |
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- 3-acetyl-6-hydroxy-(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan
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Synonyms |
3-Acetylmorphine, O(3)-monoacetylmorphine |
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CAS Number |
5140-28-3 Y |
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PubChem (CID) |
5462504 |
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ChemSpider |
4575431 Y |
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Chemical and physical data |
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Formula |
C19H21NO4 |
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Molar mass |
327.1471 g/mol |
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3D model (Jmol) |
Interactive image |
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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
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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 YKey:GMLREHXYJDLZOU-LEPYJNQMSA-N Y
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(verify) |
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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 potent, centrally acting morphine derivative and has important analgesic properties. [1] [2] [3]
![](../I/m/3-MAM-6-Sulphur.svg.png)
3-MAM-6-Sulfate (M3A6S)
![](../I/m/Acetyl_groups_of_heroin.svg.png)
Acetyl groups of heroin. In 3-MAM lower group is changed to
hydrogen making
hydroxyl-group in 6-position.
References
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MOR |
- PAMs: BMS-986121
- BMS-986122
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DOR | |
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KOR |
- Agonists: 6'-GNTI
- 8-CAC
- 18-MC
- 14-Methoxymetopon
- β-Chlornaltrexamine
- β-Funaltrexamine
- Adrenorphin (metorphamide)
- Akuuamicine
- Alazocine
- Allomatrine
- Asimadoline
- BAM-12P
- BAM-18P
- BAM-22P
- Big dynorphin
- Bremazocine
- BRL-52537
- Butorphan
- Butorphanol
- BW-373U86
- Cebranopadol
- Ciprefadol
- CR665
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Diamorphine (heroin)
- Diacetylnalorphine
- Difelikefalin
- Dihydroetorphine
- Dihydromorphine
- Diprenorphine
- Dynorphin A
- Dynorphin B (rimorphin)
- Eluxadoline
- Enadoline
- Eptazocine
- Erinacine E
- Ethylketazocine
- Etorphine
- Fedotozine
- Fentanyl
- Gemazocine
- GR-89696
- GR-103545
- Hemorphin-4
- Herkinorin
- HS665
- Hydromorphone
- HZ-2
- Ibogaine
- ICI-199,441
- ICI-204,448
- Ketamine
- Ketazocine
- Laudanosine
- Leumorphin (dynorphin B-29)
- Levallorphan
- Levomethorphan
- Levorphanol
- Lexanopadol
- Lofentanil
- LPK-26
- Lufuradom
- Matrine
- MB-1C-OH
- Menthol
- Metazocine
- Metkefamide
- Mianserin
- Mirtazapine
- Morphine
- Moxazocine
- MR-2034
- N-MPPP
- Nalbuphine
- Nalbuphine sebacate
- NalBzOH
- Nalfurafine
- Nalmefene
- Nalodeine (N-allylnorcodeine)
- Nalorphine
- Naltriben
- Niravoline
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- Noribogaine
- Norketamine
- O-Desmethyltramadol
- Oripavine
- Oxilorphan
- Oxycodone
- Pentazocine
- Pethidine (meperidine)
- Phenazocine
- Proxorphan
- Racemethorphan
- Racemorphan
- RB-64
- Salvinorin A (salvia)
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- Samidorphan
- SKF-10047
- Spiradoline (U-62,066)
- TH-030418
- Thienorphine
- Tifluadom
- Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
- U-50,488
- U-54,494A
- U-69,593
- Xorphanol
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NOP | |
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Unsorted | |
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Others |
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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See also: Peptide receptor modulators |