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Hydromorphinol Systematic (IUPAC) name 3,6,14-trihydroxy- (5α,6α)- 4,5- epoxy- 17-methylmorphinan Identifiers CAS number 2183-56-4 2190-27-4 ATC code None PubChem CID 5463858 Chemical data Formula C17H21NO4  Mol. mass 303.35 g/mol SMILES eMolecules & PubChem Synonyms Hydromorphinol, 14-hydroxy-7,8-dihydromorphine, RAM-320 Therapeutic considerations Pregnancy cat.  ? Legal status Schedule I (US) Hydromorphinol (RAM-320, 14-Hydroxydihydromorphine) is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.[1] It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is more potent and has a steeper dose-response curve and longer half-life.[2] It is used in medicine as the bitartrate salt (free base conversion ratio 0.643, molecular weight 471.5) and hydrochloride (free base conversion ratio 0.770, molecular weight 393.9) Hydromorphinol was developed in Austria in 1932. Hydromorphinol is metabolised mainly in the liver in the same fashion as many other opioids and is itself a minor active metabolite of 14-Hydroxydihydrocodeine, an uncommonly-used opiate. It is distributed under the trade name Numorphan in some countries, whereas this trade name is used for oxymorphone much more commonly. It is controlled under the Single Convention On Narcotic Drugs and the laws governing habit-forming substances in each country, such as the Controlled Substances Act of 1970 of the United States (Schedule I/Narcotic), the Betäubungsmittelgesetz (BtMG) of Germany, UK Misuse of Drugs Act, the Suchtgiftverordnung of Austria and others. See also N-Phenethylhydromorphinol (RAM-378) References ^ Weiss U, Daum SJ. Derivatives of Morphine. IV. 14-Hydroxymorphine and 14-Hydroxydihydromorphine. Journal of Medicinal Chemistry. 1965 Jan;8:123-5. PMID 14287245 ^ Plummer JL, Cmielewski PL, Reynolds GD, Gourlay GK, Cherry DA. Influence of polarity on dose-response relationships of intrathecal opioids in rats. Pain. 1990 Mar;40(3):339-47. PMID 2326098 v • d • e Opioids (N02A) Opium and Poppy straw derivatives Crude opiate extracts/ whole opium products Compote/Kompot/Polish heroin · Diascordium · B & O Supprettes · Dover's powder · Laudanum · Mithridate · Opium · Paregoric · Poppy straw concentrate · Poppy tea · Smoking opium · Theriac Natural Opiates Opium Alkaloids see also: Components of Opium Codeine · Morphine · Oripavine · Pseudomorphine · Thebaine Alkaloid Salts Mixtures Pantopon · Papaveretum (Omnopon) · Tetrapon Semisynthetics Morphine Family 2-(p-Nitrophenyl)-4-isopropylmorphine  · 14-Hydroxymorphine · 14β-Hydroxymorphine · 14β-Hydroxymorphone · 2,4-Dinitrophenylmorphine · 6-Methyldihydromorphine · 6-Methylenedihydrodesoxymorphine · 6-Acetyldihydromorphine/6-Monoacetyldihydromorphine · Acetyldihydromorphine · Azidomorphine · Chlornaltrexamine · Dihydrodesoxymorphine (Desomorphine) · Dihydromorphine · Ethyldihydromorphine · Hydromorphinol · Methyldesorphine · N-Phenethylnormorphine · Pseudomorphine · RAM-378 3,6 Diesters of Morphine Acetylpropionylmorphine · Acetylbutyrylmorphine · Diacetyldihydromorphine (Dihydroheroin) · Diacetyldibenzoylmorphine · Dibutyrylcodeine · Dibutyrylmorphine · Dibenzoylmorphine · Diformylmorphine · Dipropanoylmorphine · Heroin (Diacetylmorphine) · Nicomorphine · Tetrabenzoylmorphine · Tetrabutyrylmorphine Codeine-Dionine Family 14-Hydroxydihydrocodeine · Acetylcodeine · Benzylmorphine · Codeine methylbromide · Desocodeine · Dimethylmorphine (Methocodeine) · Methyldihydromorphine (Dihydroheterocodeine) · Ethylmorphine (Dionine) · Heterocodeine · Isocodeine · Isopropylmorphine · Morpholinylethylmorphine (Pholcodine) · Myrophine · Nalodeine · Transisocodeine Morphinones & Morphols 1-Bromohydrocodone · 1-Bromooxycodone · 1-Chlorohydrocodone · 1-Chlorooxycodone · 1-Iodohydrocodone · 1-Iodooxycodone · 14-Cinnamoyloxycodeinone · 14-Ethoxymetopon · 14-Methoxymetopon · 14β-Hydroxymorphone · 14-O-Methyloxymorphone · 14-Phenylpropoxymetopon · 7-Spiroindanyloxymorphone · 8,14-Dihydroxydihydromorphinone · Acetylmorphone · α-hydrocodol · Bromoisopropropyldihydromorphinone · Codeinone · Codorphone · Codol · Codoxime · Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) · Ethyldihydromorphinone · Hydrocodol · Hydrocodone · Hydromorphinone · Hydromorphol · Hydromorphone · Hydroxycodeine · Isopropropyldihydrocodeinone · Isopropropyldihydromorphinone · Methyldihydromorphinone · Metopon · Morphenol · Morphinol · Morphinone · Morphol · N-Phenethyl-14-ethoxymetopon · Oxycodone · Oxymorphol · Oxymorphinol · Oxymorphone · Pentamorphone · Semorphone Morphides α-chlorocodide (Alphachlorocodide/Chlorocodide)  · α-chloromorphide · 3-Bromomorphide · Bromocodide · Bromomorphide (8-Bromomorphide) · Chlorocodide · Chloromorphide ·  · Codide · Fluorocodide (8-Fluorocodide) · Fluormorphide  · Iodocodide  · Iodomorphide (8-Iodomorphide)  · Morphide Dihydrocodeine Series 14-hydroxydihydrocodeine · Acetyldihydrocodeine · Dihydrocodeine · Dihydrodesoxycodeine/Desocodeine · Dihydroisocodeine · Nicocodeine · Nicodicodeine Nitrogen Morphine Derivatives 1-Nitrocodeine · 2-Nitrocodeine · 1-Nitromorphine · 2-Nitromorphine · Codeine-N-Oxide · Heroin-N-Oxide · Hydromorphone-N-Oxide · Morphine-N-Oxide Hydrazones Acetylmorphazone · Hydromorphazone · Morphazone · Oxymorphazone  Halogenated Morphine Derivatives 1-Bromocodeine · 2-Bromocodeine · 1-Bromodiacetylmorphine · 2-Bromodiacetylmorphine · 1-Bromodihydrocodeine · 2-Bromodihydrocodeine · 1-Bromodihydromorphine · 2-Bromodihydromorphine · 1-Bromomorphine · 2-Bromomorphine · 1-Chlorocodeine · 2-Chlorocodeine · 1-Chlorodiacetylmorphine · 2-Chlorodiacetylmorphine · 1-Chlorodihydrocodeine · 2-Chlorodihydrocodeine · 1-Chlorodihydromorphine · 2-Chlorodihydromorphine · 1-Chloromorphine · 2-Chloromorphine · 1-Fluorocodeine · 2-Fluorocodeine · 1-Fluorodiacetylmorphine · 2-Fluorodiacetylmorphine · 1-Fluorodihydrocodeine · 2-Fluorodihydrocodeine · 1-Fluorodihydromorphine · 2-Fluorodihydromorphine · 1-Fluoromorphine · 2-Fluoromorphine · 3-Fluoromorphine · 1-Iodocodeine · 2-Iodocodeine · 1-Iododiacetylmorphine · 2-Iododiacetylmorphine · 1-Iododihydrocodeine · 2-Iododihydrocodeine · 1-Iododihydromorphine · 2-Iododihydromorphine · 1-Iodomorphine · 2-Iodomorphine · Chlorethylmorphine Others Pholcodine Active Opiate Metabolites Codeine-N-Oxide (Genocodeine) · Dihydromorphine-6-glucuronide · Hydromorphone-N-Oxide · Heroin-7,8-Oxide · Morphine-6-glucuronide · 6-Acetylmorphine · Morphine-N-Oxide (Genomorphine) · Naltrexol · Norcodeine · Normorphine Morphinans Morphinan Series 4-chlorophenylpyridomorphinan · Cyclorphan · Dextrallorphan · Dimemorfan · Levargorphan · Levallorphan · Levorphanol · Levorphan · Levophenacylmorphan · Levomethorphan · Norlevorphanol · N-Methylmorphinan · Oxilorphan · Phenomorphan · Methorphan / Racemethorphan · Morphanol / Racemorphanol · Ro4-1539 · Stephodeline · Xorphanol Others 1-Nitroaknadinine · 14-episinomenine · 5,6-Dihydronorsalutaridine · 6-Ketonalbuphine · Aknadinine · Butorphanol · Cephakicine · Cephasamine · Cyprodime · Drotebanol · Fenfangjine G · Nalbuphine · Sinococuline · Sinomenine (Cocculine) · Tannagine Benzomorphans 5,9-DEHB · Alazocine · Anazocine · Bremazocine · Cogazocine · Cyclazocine · Dezocine · Eptazocine · Etazocine · Ethylketocyclazocine · Fluorophen · Ketazocine · Metazocine · Pentazocine · Phenazocine · Quadazocine · Thiazocine · Tonazocine · Volazocine · Zenazocine 4-Phenylpiperidines Pethidines (Meperidines) 4-Fluoromeperidine · Allylnorpethidine · Anileridine · Benzethidine · Carperidine · Difenoxin · Diphenoxylate · Etoxeridine (Carbetidine) · Furethidine · Hydroxypethidine (Bemidone) · Hydroxymethoxypethidine · Morpheridine · Oxpheneridine (Carbamethidine) · Meperidine-N-Oxide · Pethidine (Meperidine) · Pethidine Intermediate A · Pethidine Intermediate B (Norpethidine) · Pethidine Intermediate C (Pethidinic Acid) · Pheneridine · Phenoperidine · Piminodine · Properidine (Ipropethidine) · Sameridine Prodines Allylprodine · Isopromedol · Meprodine (α-meprodine / β-meprodine) · MPPP (Desmethylprodine) · PEPAP · Prodine (α-prodine / β-prodine) · Prosidol · Trimeperidine (Promedol) Ketobemidones Acetoxyketobemidone · Droxypropine · Ketobemidone · Methylketobemidone · Propylketobemidone Others Alvimopan · Loperamide · Picenadol Open Chain Opioids Amidones Dextromethadone · Dextroisomethadone · Dipipanone · Hexalgon (Norpipanone) · Isomethadone · Levoisomethadone · Levomethadone · Methadone · Methadone intermediate · Normethadone · Norpipanone · Phenadoxone (Heptazone) · Pipidone Methadols Dimepheptanol (Racemethadol) · Levacetylmethadol · Noracetylmethadol Moramides Dextromoramide · Levomoramide · Moramide intermediate · Racemoramide Thiambutenes Diethylthiambutene · Dimethylthiambutene · Ethylmethylthiambutene · Piperidylthiambutene · Pyrrolidinylthiambutene · Thiambutene · Tipepidine Phenalkoxams Dextropropoxyphene (Propoxyphene) · Dimenoxadol · Dioxaphetyl Butyrate · Levopropoxyphene · Norpropoxyphene Ampromides Diampromide · Phenampromide · Propiram Others IC-26 · Isoaminile · Lefetamine · R-4066 Anilidopiperidines 3-Allylfentanyl · 3-Methylfentanyl · 3-Methylthiofentanyl · 4-Phenylfentanyl · Alfentanil · α-methylacetylfentanyl · α-methylfentanyl · α-methylthiofentanyl · Benzylfentanyl · β-hydroxyfentanyl · β-hydroxythiofentanyl · β-methylfentanyl · Brifentanil · Carfentanil · Fentanyl · Lofentanil · Mirfentanil · Ocfentanil · Ohmefentanyl · Parafluorofentanyl · Phenaridine · Remifentanil · Sufentanil · Thenylfentanyl · Thiofentanyl · Trefentanil Oripavine derivatives 6,14-Endoethenotetrahydrooripavine · 7-PET · Acetorphine · Alletorphine · BU-48 · Buprenorphine · Butorphine · Cyprenorphine · Dihydroetorphine · Diprenorphine (M5050) · Etorphine · 18,19-Dehydrobuprenorphine (HS-599) · N-cyclopropylmethyl-noretorphine · Nepenthone · Norbuprenorphine · Thevinone · Thienorphine Phenazepanes Ethoheptazine · Meptazinol · Metheptazine · Metethoheptazine · Proheptazine Pirinitramides Bezitramide · Piritramide Benzimidazoles Clonitazene · Etonitazene · Nitazene Indoles 18-MC · 7-Acetoxymitragynine · 7-Hydroxymitragynine · Akuammidine · Akuammine · Eseroline · Hodgkinsine · Ibogaine · Mitragynine · Noribogaine · Pericine · ψ-Akuammigine Diphenylmethylpiperazines BW373U86 · DPI-221 · DPI-287 · DPI-3290 · SNC-80 Opioid peptides see also: The Opioid Peptides Casomorphin · DADLE · DALDA · DAMGO · Dermenkephalin · Dermorphin · Deltorphin · DPDPE · Dynorphin · Endomorphin · Endorphin · Enkephalin · Gliadorphin · Morphiceptin · Nociceptin · Octreotide · Opiorphin · Rubiscolin · TRIMU 5 Others 3-(3-Methoxyphenyl)-3-ethoxycarbonyltropane · AH-7921 • Azaprocin · BDPC · Bisnortilidine · BRL-52537 · Bromadoline • C-8813 · Ciramadol · Doxpicomine • Enadoline · Faxeladol · GR-89696 · Herkinorin · ICI-199,441 · ICI-204,448 · J-113,397 · JTC-801 · LPK-26 · Methopholine · N-Desmethylclozapine · NNC 63-0532 · Nortilidine · O-Desmethyltramadol · Phenadone · Prodilidine · Profadol · Ro64-6198 · Salvinorin A · SB-612,111 · SC-17599 · RWJ-394,674 · TAN-67 · Tapentadol · Tecodine · Tifluadom · Tilidine · Tramadol · Trimebutine · U-50,488 · U-69,593 · Viminol · W-18 · Opioid Antagonists & Inverse-Agonists 5'-Guanidinonaltrindole · β-Funaltrexamine · 6β-Naltrexol · Alvimopan · Amiphenazole · Binaltorphimine · Chlornaltrexamine · Clocinnamox · Cyclazocine · Cyprodime · Diprenorphine (M5050) · Fedotozine · JDTic · Levallorphan · Methocinnamox · Methylnaltrexone · Nalfurafine · Nalmefene · Nalmexone · Naloxazone · Naloxonazine · Naloxone · Naloxone benzoylhydrazone · Nalorphine · Naltrexone · Naltriben · Naltrindole · Norbinaltorphimine · Oxilorphan · S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM) This analgesic-related article is a stub. 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