- Morphinan
-
Morphinan 
MorphinanSystematic name17-Azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trieneOther names1,2,3,9,10,10a-Hexahydro-10,4a(4H)-iminoethanophenanthreneIdentifiers CAS number 468-10-0 
PubChem 11947744 (1R,9R,10R), 614838, 21176124 (1S,9R,10R), 6857497 (1S,9S,10R), 18350845 (hydrochloride), 20678913 (1S,9S,10R),(hydrochloride) ChemSpider 5256833 (1R,9R,10R) 
, 534418 , 10122060 (1S,9R,10R) ChEBI CHEBI:35649 Beilstein Reference 1375527 Jmol-3D images Image 1 - C1CCC23CCNC(CC4=C2C=CC=C4)C3C1
- InChI=1S/C16H21N/c1-2-6-13-12(5-1)11-15-14-7-3-4-8-16(13,14)9-10-17-15/h1-2,5-6,14-15,17H,3-4,7-11H2/t14-,15-,16+/m0/s1
Key: INAXVFBXDYWQFN-HRCADAONSA-N
InChI=1S/C16H21N/c1-2-6-13-12(5-1)11-15-14-7-3-4-8-16(13,14)9-10-17-15/h1-2,5-6,14-15,17H,3-4,7-11H2
Key: INAXVFBXDYWQFN-UHFFFAOYSA-N
Properties Molecular formula C16H21N Molar mass 227.34 g/mol Density 1.58 g/cm3 Boiling point 115±0.05°C (liquid oil)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Morphinan is the base chemical structure of a large chemical class of psychoactive drugs, consisting of opioid analgesics, cough suppressants, and dissociative hallucinogens, among others.
Chemical Derivatives
Immediate derivatives of morphinan include:
- Dextrallorphan
- Dextromethorphan
- Dextrorphanol
- Dimemorfan
- Levallorphan
- Levofurethylnormorphanol
- Levomethorphan
- Levophenacylmorphan
- Levorphanol
- Methorphan
- Morphanol
- Oxilorphan
- Phenomorphan
- Xorphanol
More distant of derivatives include:
As well as the following:
- Morphine (and analogues)
Chemical Relatives
The following are related to morphinan:
References
Anesthetic: General anesthetics (N01A) Inhalation OthersInjection OthersCough and cold preparations (R05) Expectorants Mucolytics Acetylcysteine • Ambroxol • Bromhexine • Carbocisteine • Domiodol • Dornase alfa • Eprazinone • Erdosteine • Letosteine • Mesna • Neltenexine • Sobrerol • Stepronin • TioproninCough suppressants Acetyldihydrocodeine • Benzylmorphine • Codeine • Dextromethorphan • Diacetylmorphine • Dihydrocodeine • Dimemorfan • Droxypropine • Ethylmorphine • Hydrocodone • Hydromorphone • Isoaminile • Laudanum • Levomethadone • Levopropoxyphene • Methadone • Nicocodeine • Nicodicodeine • Normethadone • Noscapine • Pholcodine • Thebacon • Tipepidine • ZipeprolOtherBenzonatate • Benproperine • Bibenzonium bromide • Butamirate • Clobutinol • Clofedanol • Cloperastine • Diphenhydramine • Dibunate • Dimethoxanate • Dropropizine • Fedrilate • Glaucine • Levodropropizine • Meprotixol • Morclofone • Nepinalone • Oxolamine • Oxeladin • Pentoxyverine • Pipazetate • Prenoxdiazine • PiperidioneHallucinogens Psychedelics
5-HT2AR agonists- Lysergamides: AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAM-57
- Diallyllysergamide
- Ergometrine (Ergonovine, Ergobasine)
- ETH-LAD
- LAE-32
- LSA (Ergine, Lysergamide)
- LSD
- LSH
- LPD-824
- LSM-775
- Lysergic Acid 2-Butyl Amide
- Lysergic Acid 2,4-Dimethylazetidide
- Lysergic Acid 3-Pentyl Amide
- Methylergometrine
- Methylisopropyllysergamide
- Methysergide
- MLD-41
- PARGY-LAD
- PRO-LAD;
- Phenethylamines: Aleph
- 2C-B
- 2C-B-Dragonfly
- 2C-B-FLY
- 2C-C-FLY
- 2C-D-FLY
- 2C-E-FLY
- 2C-I-FLY
- 2CBFly-NBOMe
- 2C-T-7-FLY
- 2C-C
- 2C-C-NBOMe
- 2C-CN-NBOMe
- 2C-D
- 2CD-5EtO
- 2C-D-NBOMe
- 2C-E
- 2C-EF
- 2C-E-NBOMe
- 2C-F
- 2C-F-NBOMe
- 2C-G
- 2C-G-NBOMe
- 2C-H-NBOMe
- 2C-I
- 2C-N
- 2C-N-NBOMe
- 2C-O
- 2C-O-4
- 2C-P
- 2C-T
- 2C-T-2
- 2C-T-4
- 2C-T-4-NBOMe
- 2C-T-7
- 2C-T-7-NBOH
- 2C-T-8
- 2C-T-9
- 2C-T-13
- 2C-T-15
- 2C-T-17
- 2C-T-21
- 2C-TFM
- 2C-TFM-NBOMe
- 2C-YN
- 2CBCB-NBOMe
- 25B-NBOMe
- 25I-NBMD
- 25I-NBOH
- 25I-NBOMe
- 3C-E
- 3C-P
- 5-APB
- 5-APDB
- 6-APB
- 6-APDB
- Br-DFLY
- DESOXY
- DMMDA
- DMMDA-2
- DOB
- DOB-FLY
- DOM-FLY
- DOC
- DOEF
- DOET
- DOF
- DOI
- DOM
- DON
- DOPR
- DOTFM
- Escaline
- Ganesha
- HOT-2
- HOT-7
- HOT-17
- IAP
- Isoproscaline
- Jimscaline
- Lophophine
- MDA
- MDEA
- MDMA
- MMA
- MMDA
- MMDA-2
- MMDA-3a
- MMDMA
- Macromerine
- Mescaline
- Methallylescaline
- NBOMe-mescaline
- Proscaline
- TCB-2
- TFMFly
- TMA;
- Piperazines: pFPP
- TMFPP;
- Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine
- 2,N,N-TMT
- 4-HO-5-MeO-DMT
- 4-Acetoxy-DET
- 4-Acetoxy-DIPT
- 4-Acetoxy-DMT
- 4-Acetoxy-DPT
- 4-Acetoxy-MiPT
- 4-HO-DPT
- 4-HO-MET
- 4-Propionyloxy-DMT
- 4-HO-MPMI
- 5-Me-MIPT
- 5-N,N-TMT
- 5-AcO-DMT
- 5-MeO-2,N,N-TMT
- 5-MeO-α,N,N-TMT
- 5-MeO-α-ET
- 5-MeO-α-MT
- 5-MeO-DALT
- 5-MeO-DET
- 5-MeO-DIPT
- 5-MeO-DMT
- 5-MeO-DPT
- 5-MeO-EiPT
- 5-MeO-MET
- 5-MeO-MIPT
- 5-MeO-MPMI
- 7,N,N-TMT
- α,N,N-TMT
- α-ET
- α-MT
- AL-37350A
- Baeocystin
- Bufotenin
- DALT
- DBT
- DCPT
- DET
- DIPT
- DMT
- DPT
- EiPT
- Ethocin
- Ethocybin
- Iprocin
- MET
- Miprocin
- MIPT
- Norbaeocystin
- PiPT
- Psilocin
- Psilocybin;
- Others: AL-38022A
- Ibogaine
- Noribogaine
- Voacangine
Dissociatives
NMDAR antagonists- Arylcyclohexylamines: 3-MeO-PCP
- 4-MeO-PCP
- Dieticyclidine
- Esketamine
- Eticyclidine
- Gacyclidine
- Ketamine
- Methoxetamine
- Neramexane
- Phencyclidine
- PCPr
- Rolicyclidine
- Tenocyclidine
- Tiletamine;
- Morphinans: Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Methorphan (Racemethorphan)
- Racemorphan;
- Others: 2-MDP
- 8A-PDHQ
- Aptiganel
- Dexoxadrol
- Dizocilpine (MK-801)
- Etoxadrol
- Ibogaine
- Midafotel
- NEFA
- Nitrous Oxide
- Noribogaine
- Perzinfotel
- Remacemide
- Selfotel
- Xenon
Deliriants
mAChR antagonists- 3-Quinuclidinyl benzilate
- Atropine
- Benactyzine
- Benzatropine
- Benzydamine
- Biperiden
- Brompheniramine
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Chlorpheniramine
- Chloropyramine
- Clemastine
- CS-27349
- Cyclizine
- Cyproheptadine
- Dicyclomine (Dicycloverine)
- Dimenhydrinate
- Diphenhydramine
- Ditran
- Doxylamine
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Elemicin
- Flavoxate
- Hydroxyzine
- Hyoscyamine
- Meclizine
- Myristicin
- N-Ethyl-3-piperidyl benzilate
- N-Methyl-3-piperidyl benzilate
- Pyrilamine
- Orphenadrine
- Oxybutynin
- Pheniramine
- Phenyltoloxamine
- Procyclidine
- Promethazine
- Scopolamine (Hyoscine)
- Tolterodine
- Trihexyphenidyl
- Tripelennamine
- Triprolidine
- WIN-2299
Miscellaneous - Apomorphine
- Bromocriptine
- Cabergoline
- Lisuride
- Memantine
- Pergolide
- Piribedil
- Pramipexole
- Ropinirole
- Rotigotine
- Butane
- Chloroform
- Diethyl Ether (Ether)
- Enflurane
- Freon
- Gasoline (Petrol)
- Kerosene (Paraffin)
- Propane
- Toluene
κOR agonists- 2-EMSB
- 2-MMSB
- Alazocine
- Bremazocine
- Butorphanol
- Cyclazocine
- Cyprenorphine
- Dextrallorphan
- Dezocine
- Enadoline
- Herkinorin
- HZ-2
- Ibogaine
- Ketazocine
- Metazocine
- Nalbuphine
- Nalorphine
- Noribogaine
- Pentazocine
- Phenazocine
- Salvinorin A
- Spiradoline
- Tifluadom
- U-50,488
- U-69,593
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Noscapine (Narcotine)
OthersOpioids Opium and
poppy straw
derivativesCrude opiate extracts/
whole opium productsCompote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac
Natural opiates Opium alkaloids
see also: Components of opiumCodeine • Morphine • Oripavine • Pseudomorphine • Thebaine
Alkaloid salts mixtures Semisynthetics
including
Bentley compoundsMorphine family 3,6-diesters of morphine Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine
Codeine-dionine family Morphinones and morphols 14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone
Morphides Dihydrocodeine series 14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine
Nitrogen morphine derivatives Hydrazones Halogenated morphine derivatives 1-Iodomorphine
Active opiate
metabolitesMorphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine
Morphinans Morphinan series Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol
Others Benzomorphans 8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine
4-Phenylpiperidines Pethidines
(Meperidines)4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine
Prodines Ketobemidones Others Open chain
opioidsAmidones Methadols Moramides Dextromoramide • Levomoramide • Racemoramide
Thiambutenes Phenalkoxams Ampromides Others IC-26 • Isoaminile • Lefetamine • R-4066
Anilidopiperidines 3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil
Oripavine
derivativesPhenazepanes Pirinitramides Benzimidazoles Indoles Diphenylmethylpiperazines Opioid peptides
see also: Opioid neuropeptidesAdrenorphin • Amidorphin • Casomorphin • DADLE • DAMGO • Dermorphin • Dynorphin • Endomorphin • Endorphins • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5
Others AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18
Opioid antagonists
&
inverse agonists5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexol-d4 • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan
List of opioidsCategories:- Morphinans
- Opioids
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