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Encyclopedia > Monoacetylmorphine

6-monoacetylmorphine (6-MAM) is one of 2 active metabolites of heroin (diacetylmorphine), the other being the much less active 3-monoacetylmorphine (3-MAM). A metabolite is the product of metabolism. ... Heroin, also known as diamorphine (BAN) or diacetylmorphine (INN), is a semi-synthetic opioid. ...


Along with morphine, 6-MAM is rapidly created from heroin in the body, and is excreted in the urine. Since 6-MAM is a unique metabolite to heroin, its presence in the urine confirms that heroin was the opiate used. This is significant because on a urine immunoassay drug screen, the test typically tests for morphine, which is a metabolite of a number of legal and illegal opiates such as codeine, morphine sulphate, and heroin. 6-MAM remains in the urine for no more than 24 hours so a urine specimen must be collected soon after the last heroin use, but the presence of 6-MAM guarantees that heroin was in fact used as recently as within the last day. 6-MAM is naturally found in the brain [1], but in such small quantities that detection of this compound in urine virtually guarantees that heroin has been recently been consumed. An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ... Morphine (INN) (IPA: ) is a potent opiate analgesic drug and is the principal active agent in opium. ... Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ...


In contrast to heroin, 6-MAM actively binds with μ-opioid receptors; diacetylmorphine (heroin) itself actually has very weak affinity to μ-opioid receptors because the 3-hydroxy group which is essential for binding to the receptor is masked by the acetyl group, however heroin is rapidly metabolised by esterase enzymes in the brain, giving it an extremely short half life. The high lipid solubility of heroin causes its powerful effects, because it delivers a higher concentration of morphine past the blood brain barrier much quicker then morphine alone. [2] To meet Wikipedias quality standards, this article may require cleanup. ... The blood-brain barrier is a physical barrier between the blood vessels in the central nervous system, and the central nervous system itself. ...


6-monoacetylmorphine already has a free 3-hydroxy group and shares the high lipophilicity of heroin, so it penetrates the brain just as quickly and does not need to be deacetylated at the 3-position in order to be bioactivated; this makes 6-monoacetylmorphine somewhat more potent than heroin, [3] but it is rarely encountered as an illicit drug due to the difficulty in selectively acetylating morphine at the 6-position without also acetylating the 3-position. This can however be accomplished by using acetic acid with an appropriate catalyst to carry out the acetylation, rather than acetic anhydride, as acetic acid is not a strong enough acetylating agent to acetylate the phenolic 3-hydroxy group but is able to acetylate the 6-hydroxy group, thus selectively producing 6-MAM rather than heroin.


Image:6-MAM.png


6-acetylmorphine


CAS# 2784-73-8


References

  1. ^ Weitz CJ, Lowney LI, Faull KF, Feistner G, Goldstein A. 6-Acetylmorphine: a natural product present in mammalian brain. Proceedings of the National Acadamy of Science U S A. 1988 Jul;85(14):5335-8.
  2. ^ Inturrisi CE, Schultz M, Shin S, Umans JG, Angel L, Simon EJ. Evidence from opiate binding studies that heroin acts through its metabolites. Life Sciences. 1983;33 Suppl 1:773-6.
  3. ^ Tasker RA, Vander Velden PL, Nakatsu K. Relative cataleptic potency of narcotic analgesics, including 3,6-dibutanoylmorphine and 6-monoacetylmorphine. Progress in Neuropsychopharmacology and Biological Psychiatry. 1984;8(4-6):747-50.


[edit]Opioids

Acetorphine, Acetyldihydrocodeine, Acetylmorphone, Alfentanil, Anileridine, Bemidone, Benzylmorphine, Buprenorphine, Butorphanol, Carfentanil, Clonitazene, Codeine, Codeinone, Codeine-N-Oxide, Cyclazocine, Cyclorphan, Desomorphine, Dextropropoxyphene, Dezocine, Diacetyldihydromorphine, Diamorphine (Heroin), Diethylthiambutene, Difenoxin, Dihydrocodeine, Dihydromorphine, Dihydrocodeinone enol acetate, Dihydroetorphine, Dihydroisocodeine, Dimethylthiambutene, Diphenoxylate, Dipropanoylmorphine, Ethylketocyclazocine, Ethylmorphine, Etonitazene, Etorphine, Fentanyl, Hydrocodone, Hydromorphone, Isomethadone, Ketobemidone, Laudanum, Lefetamine, Levallorphan, Levomethorphan, Levo-alphacetylmethadol, Loperamide, Meptazinol, Metazocine, Methadone, Monoacetylmorphine, Morphine, Morphinone, Morphine-N-Oxide, Morphine-6-glucuronide, MPPP, Myorphine, Nalbuphine, Nicocodeine, Nicodicodeine, Nicomorphine, Norcodeine, Ohmefentanyl, Oxycodone, Oxymorphone, Pentazocine, PEPAP, Pethidine (Meperidine), Phenadoxone, Phenazocine, Phenoperidine, Pholcodeine, Piminodine, Racemethorphan, Remifentanil, Sufentanil, Thebaine, Thiofentanil, Tramadol An opioid is a chemical substance that has a morphine like action in the body. ... Acetyldihydrocodeine is an opiate derivative developed as a cough suppressant and analgesic. ... Acetylmorphone (Dihydromorphinone acetate) is an opiate analogue that is an acetylated derivative of hydromorphone which was developed in the early 1900s as a potential cough suppressant and analgesic. ... Alfentanil (Alfenta) is a parenteral short-acting opioid painkiller, used for anaesthesia in surgery. ... Anileridine (Leritine®) is a synthetic opioid and strong analgesic medication. ... Buprenorphine, also colloquially referred to as bupe, is an opioid drug with partial agonist and antagonist actions. ... Butorphanol (INN) is a morphinan-type synthetic opioid analgesic marketed in the US under the trade name Stadol. ... Carfentanil, also Carfentanyl, is an analogue of the popular opioid Fentanyl, and is currently the most potent opioid known [Actually Ohmefentanil is 13,000X morphine]. It has a quantitative potency approximately 10,000 times that of morphine and 100 times that of fentanyl (activity in humans starting at about 1... Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ... Codeinone is a strong Opiod. ... Dextropropoxyphene is an analgesic in the opioid category. ... Diacetyldihydromorphine (Paralaudin, Dihydroheroin) is a potent opiate derivative which is rarely used in some countries for the treatment of strong pain such as that caused by terminal cancer, as a more potent form of diamorphine. ... Heroin, also known as diamorphine (BAN) or diacetylmorphine (INN), is a semi-synthetic opioid. ... Dihydrocodeine, also called DHC and Paracodeine and by the brand names of SS Bron, Drocode, Paracodin, Codidol, Didor Continus, Dicogesic, and DF-118 amongst others, is a semi-synthetic opioid analgesic prescribed for postoperative pain, severe dyspnea, or as an antitussive. ... Dihydromorphine is a semi-synthetic opioid invented in Germany in the first years of the twentieth century. ... The chemical structure of dihydrocodeinone enol acetate Dihydrocodeinone Enol Acetate, or Thebacon, formerly marketed as its hydrochloride salt under the trade name Acedicon, is a semisynthetic opioid once used as an antitussive, primarily in Europe. ... On opiod agonist used for the treatment of diarrhea. ... Dipropanoylmorphine is the 3,6-dipropanoyl ester of morphine. ... Ethylmorphine is a drug in the class of both opiates (representing a minor synthetic change from morphine) and opioids (being effective in the CNSs opioid reception system) . Its effects in humans mainly stem from its metabolic conversion to morphine. ... Etonitazene, (2-(p-Ethoxybenzyl)-1-diethylaminoethyl-5-nitrobenzimidazole), is a schedule I opiate. ... Etorphine (Immobilon® or M99) is a synthetic cousin of morphine and 1000 - 80,000 times more powerful. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... It has been suggested that Vicodin be merged into this article or section. ... Hydromorphone is a drug used to relieve moderate to severe pain. ... Ketobemidone structure Ketobemidone is a powerful opioid analgesic. ... Laudanum is an opium tincture, sometimes sweetened with sugar and also called wine of opium. ... Lefetamine is a psychoactive drug which has effects similar to both morphine and methylphenidate. ... Levomethorphan is an optical isomer of dextromethorphan. ... Levo-alpha-acetyl-methadol (LAAM for short) is a synthetic opioid similar in structure to methadone. ... Loperamide, usually as hydrochloride, is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. ... Methadone is a synthetic opioid, used medically as an analgesic and in the treatment of narcotic addiction. ... Morphine (INN) (IPA: ) is a potent opiate analgesic drug and is the principal active agent in opium. ... Morphinone is a very strong Opiod. ... Morphine-6-glucuronide (M6G) is of more than simply academic interest, since it is the major active metabolite of morphine, and as such is the molecule responsible for much of the pain-relieving effects of morphine (and heroin and codeine). ... MPPP (1-methyl 4-phenyl 4-propionoxypiperidine) is an opioid analgesic drug. ... Nalbuphine (nalbuphine hydrochloride) is a synthetic opioid used commercially as an analgesic under a variety of trade names, including Nubain. ... // Ohmefentanyl (OMF) is related to a fentanyl analogue called 3-methyl-fentanyl (3-MF)[1],[2]. OMF is more sophisticated than 3-MF though since it also has a β-hydroxy group situated on the phenethyl tail. ... Not to be confused with oxytocin. ... Oxymorphone (Numorphan) is a powerful semi-synthetic narcotic analgesic that is derived from morphine, and is approximately 6-8 times more potent. ... Pentazocine is a synthetically-prepared narcotic drug used to treat mild to moderate pain. ... Pethidine (INN) or meperidine (USAN) (also referred to as: isonipecaine; lidol; operidine; pethanol; piridosal; Algil®; Alodan®; Centralgin®; Demerol®; Dispadol®; Dolantin®; Dolestine®; Dolosal®; Dolsin®; Mefedina®) is a fast-acting opioid analgesic drug. ... Phenoperidine is an opiod general anesthetic. ... Racemethorphan is a racemic mixture of the stereoisomers of methorphan , namely dextromethorphan , which is the active ingredient in DM cough syrups , and the lesser known levomethorphan which is described as a controlled substance in The Merck Index - likely because it has more potential for abuse than its dextro enantiomer . ... Remifentanil is a potent ultra short-acting synthetic opioid analgesic drug. ... Sufentanil is a drug that belongs to the class of drugs known as the opioid analgesic drugs. ... A minor constituent of opium, thebaine or paramorphine (C19H21NO3) is chemically similar to both morphine and codeine, but produces stimulatory rather than depressant effects. ... Tramadol (INN) (IPA: ) is an atypical opioid which is a centrally acting analgesic, used for treating moderate to severe pain. ...


 
 

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