Opium poppy (Papaver somniferum) flower
This is a list of opioids, opioid antagonists and inverse agonists.
Opium and poppy straw derivatives
Seedhead of opium poppy with white latex
Crude opiate extracts whole opium products
Natural opiates
Opium alkaloids
Structures
| Morphides | ||||
|---|---|---|---|---|
 Codeine |
 Morphine |
 Oripavine |
 Pseudomorphine |
 Thebaine |
Alkaloid salts mixtures
- Pantopon
- Papaveretum (Omnopon)
- Tetrapon
Semisynthetics including Bentley compounds
Morphine family
- 14-Hydroxymorphine [1]
- 2,4-Dinitrophenylmorphine
- 6-Methyldihydromorphine [2]
- 6-Methylenedihydrodesoxymorphine
- 6-Acetyldihydromorphine [3]
- Azidomorphine
- Chlornaltrexamine
- Chloroxymorphamine [4]
- Desomorphine (dihydrodesoxymorphine)
- Dihydromorphine
- Ethyldihydromorphine [5]
- Hydromorphinol
- Methyldesorphine
- Morphine methylbromide
- N-Phenethylnordesomorphine
- N-Phenethyl-14-ethoxymetopon
- N-Phenethylnormorphine
- 6-Nicotinoyldihydromorphine (metabolite of nicodicodeine)
- RAM-378
- Ro-1539
Structures of Morphine family
| Morphine family | ||||
|---|---|---|---|---|
 14-Hydroxymorphine |
 2,4-Dinitrophenylmorphine |
 6-Methyldihydromorphine |
 6-Methylenedihydrodesoxymorphine |
 6-Acetyldihydromorphine hydrochloride |
 Azidomorphine |
 Chlornaltrexamine |
 Chloroxymorphamine |
 Desomorphine (Dihydrodesoxymorphine) |
 Dihydromorphine |
 Ethyldihydromorphine |
 Hydromorphinol |
 Methyldesorphine |
 N-Phenethylnormorphine |
 6-nicotinoyldihydromorphine |
 RAM-378 | ||||
3,6-diesters of morphine
- Acetylpropionylmorphine
- 3,6-Dibutanoylmorphine
- Diacetyldihydromorphine (dihydroheroin, acetylmorphinol)
- Dibutyrylmorphine
- Dibenzoylmorphine (first designer drug)
- Diformylmorphine
- Dipropanoylmorphine
- Heroin (diacetylmorphine)
- Nicomorphine
Structures
| 3,6-diesters of morphine | ||||
|---|---|---|---|---|
 Acetylpropionylmorphine |
3,6-Dibutanoylmorphine |  Diacetyldihydromorphine(dihydroheroin, acetylmorphinol) | ||
 Dibutyrylmorphine |
 Dibenzoylmorphine |
 Diformylmorphine | ||
 Dipropanoylmorphine |
 Heroin(diacetylmorphine) |
 Nicomorphine | ||
Codeine-dionine family
- 6-Monoacetylcodeine
- Benzylmorphine
- Codeine methylbromide
- Desocodeine
- Dimethylmorphine (6-O-Methylcodeine)
- Ethyldihydromorphine
- Methyldihydromorphine (dihydroheterocodeine)
- Ethylmorphine (dionine)
- Heterocodeine
- Isocodeine
- Pholcodine (morpholinylethylmorphine)
- Myrophine
- Thebacon
- Transisocodeine
Structures
| Codeine-dionine family | ||||
|---|---|---|---|---|
 6-Monoacetylcodeine |
 Benzylmorphine |
 Codeine methylbromide |
 Desocodeine |
 Dimethylmorphine(6-O-Methylcodeine) |
| Ethyldihydromorphine |
 Methyldihydromorphine(dihydroheterocodeine) |
 Ethylmorphine |
 Heterocodeine |
 Isocodeine |
 Pholcodine |
 Myrophine |
 Transisocodeine | ||
Morphinones and morphols
- 14-Cinnamoyloxycodeinone
- 14-Ethoxymetopon
- 14-Methoxymetopon
- 14-Phenylpropoxymetopon
- 3-Acetyloxymorphone
- 3,14-Diacetyloxymorphone
- 7-Spiroindanyloxymorphone
- 8,14-Dihydroxydihydromorphinone
- Acetylcodone
- Acetylmorphone
- α-hydrocodol (=dihydrocodeine, )
- Benzhydrocodone
- Bromoisopropropyldihydromorphinone cas?
- Codeinone
- Codoxime
- Conorfone (codorphone)
- IBNtxA
- Thebacon (acetyldihydrocodeinone, dihydrocodeinone enol acetate)
- Hydrocodone
- Hydromorphone
- Hydroxycodeine
- Metopon (=methyldihydromorphinone)
- Morphenol
- Morphinone
- Morphol
- N-Phenethyl-14-ethoxymetopon
- Noroxymorphone
- Oxycodone
- Oxymorphol
- Oxymorphone
- Pentamorphone
- Semorphone
Structures
| Morphinones and morphols | ||||
|---|---|---|---|---|
 14-Cinnamoyloxycodeinone |
 14-Ethoxymetopon |
 14-Methoxymetopon |
 14-Phenylpropoxymetopon |
 7-Spiroindanyloxymorphone |
 8,14-Dihydroxydihydromorphinone |
 Acetylcodone |
 Acetylmorphone |
 α-hydrocodol(Dihydrocodeine) |
 Bromoisopropropyldihydromorphinone |
 Codeinone |
 Codorphone |
 Codol(Codeine Phosphate) |
 Codoxime |
 IBNtxA |
 Thebacon |
 Hydrocodone |
 Hydromorphone |
 Hydroxycodeine |
 Metopon(methyldihydromorphinone) |
 Morphenol |
 Morphinone |
 Morphol |
 N-Phenethyl-14-ethoxymetopon |
 Oxycodone |
 Oxymorphol |
 Oxymorphone |
 Pentamorphone |
 Semorphone |
|
Morphides
- α-Chlorocodide (= chlorocodide)
- β-Chlorocodide
- α-Chloromorphide (= chloromorphide)
- Bromocodide
- Bromomorphide
- Chlorodihydrocodide
- Chloromorphide
- Codide
Structures
| Morphides | ||||
|---|---|---|---|---|
 α-chlorocodide |
 β-chlorocodide |
 Bromomorphide | ||
 Chlorodihydrocodide. |
 Chloromorphide |
 Codide | ||
Dihydrocodeine series
Nitrogen morphine derivatives
- 1-Nitrocodeine cas?
- Codeine-N-oxide
- Morphine-N-oxide
Structures
| Morphides | ||||
|---|---|---|---|---|
 1-Nitrocodeine |
 Codeine-N-oxide |
 Morphine-N-oxide | ||
Hydrazones
Structures
| Hydrazones | ||||
|---|---|---|---|---|
 Oxymorphazone | ||||
Halogenated morphine derivatives
- 1-Bromocodeine
- 1-Chlorocodeine
- 1-Iodomorphine
Structures
| Other open chain opioids | ||||
|---|---|---|---|---|
1-Bromocodeine |
1-Chlorocodeine |
| ||
Active opiate metabolites
- Codeine-6-glucuronide
- Codeine-N-oxide (genocodeine)
- Heroin-7,8-oxide
- Morphine-6-glucuronide
- 3-Monoacetylmorphine
- 6-Monoacetylmorphine
- Morphine-N-oxide (genomorphine)
- Naltrexol
- Norcodeine
- Normorphine
Structures
| Active opiate metabolites | ||||
|---|---|---|---|---|
| Codeine-N-oxide |
 Heroin-7,8-oxide |
 Morphine-6-glucuronide |
 6-Monoacetylmorphine | |
| Morphine-N-oxide |
 Naltrexol |
 Norcodeine |
 Normorphine | |
Morphinans
Morphinan series
- 3-Hydroxymorphinan
- 4-Chlorophenylpyridomorphinan
- Cyclorphan
- Levargorphan
- Levorphanol
- Levophenacylmorphan
- Levomethorphan
- Methorphan (racemethorphan)
- Morphanol (racemorphanol)
- Norlevorphanol
- N-Methylmorphinan
- Oxilorphan
- Phenomorphan
- Proxorphan
- Ro4-1539
- Stephodeline Xorphanol
Structures
| Other morphinans | ||||
|---|---|---|---|---|
 4-chlorophenylpyridomorphinan |
 Cyclorphan |
 Dextrallorphan |
 Levargorphan |
 Levophenacylmorphan |
 Levomethorphan |
 Norlevorphanol |
 N-Methylmorphinan |
 Oxilorphan |
 Phenomorphan |
 Dextromethorphan levomethorphan |
 Morphanol |
 Ro4-1539 |
 Stephodeline |
 Xorphanol |
Others
- 1-Nitroaknadinine * 14-episinomenine
- 5,6-Dihydronorsalutaridine
- 6-Keto Nalbuphine
- Aknadinine
- Butorphanol
- Cephakicine
- Cephasamine
- Cyprodime
- Drotebanol
- Fenfangjine G
- Ketorfanol
- Nalbuphine
- Nalbuphone
- Tannagine
Structures
| Other Morphinans | ||||
|---|---|---|---|---|
 1-Nitroaknadinine |
 14-episinomenine |
 5,6-Dihydronorsalutaridine |
 6-Keto Nalbuphine |
 Aknadinine |
 Butorphanol |
 Cephakicine |
 Cephasamine |
 Cyprodime |
 Drotebanol |
 Fenfangjine G |
 Nalbuphine |
 Sinococuline |
 Sinomenine |
 Tannagine |
Benzomorphans
- 5,9 alpha-diethyl-2-hydroxybenzomorphan (5,9-DEHB)
- 8-Carboxamidocyclazocine (8-CAC)
- Alazocine
- Anazocine
- Bremazocine
- Butinazocine
- Carbazocine
- Cogazocine
- Cyclazocine
- Dezocine
- Eptazocine
- Etazocine
- Ethylketazocine
- Fedotozine
- Fluorophen
- Gemazocine
- Ibazocine
- Ketazocine
- Metazocine
- Moxazocine
- Pentazocine
- Phenazocine
- Quadazocine
- SKF-10047
Structures
| Benzomorphans | ||||
|---|---|---|---|---|
 5,9 alpha-diethyl-2-hydroxybenzomorphan (5,9-DEHB) |
 8-Carboxamidocyclazocine |
 Alazocine |
 Anazocine |
 Bremazocine |
 Butinazocine |
 Carbazocine |
 Cogazocine |
 Cyclazocine |
 Dezocine |
 Eptazocine |
 Etazocine |
 Ethylketocyclazocine |
 Fedotozine |
 Fluorophen |
 Gemazocine |
 Ibazocine |
 Ketazocine |
 Metazocine |
 Moxazocine |
 Pentazocine |
 Phenazocine |
 Quadazocine
|
 Thiazocine |
 Tonazocine |
 Volazocine |
 Zenazocine |
|||
4-Phenylpiperidines
Pethidines (meperidines)
- 4-Fluoropethidine
- Allylnorpethidine
- Anileridine
- Benzethidine
- Carperidine
- Difenoxin
- Diphenoxylate
- Etoxeridine (carbetidine)
- Furethidine
- Hydroxypethidine (bemidone)
- Morpheridine
- Meperidine-N-oxide
- Oxpheneridine (carbamethidine)
- Pethidine (meperidine)
- Pethidine intermediate A
- Pethidine intermediate B (norpethidine)
- Pethidine intermediate C (pethidinic acid)
- Pheneridine
- Phenoperidine
- Piminodine
- Properidine (ipropethidine)
- Sameridine
Structures
Prodines
- Allylprodine
- (α/β)-Meprodine
- Desmethylprodine (MPPP)
- PEPAP
- (α/β)-Prodine
- Prosidol
- Trimeperidine (promedol)
Structures
Ketobemidones
Structures
Others
Structures
| Other phenylpiperidines | |||
|---|---|---|---|
 Alvimopan |
 Loperamide |
 LS-115509 |
 Picenadol |
Open chain opioids
Amidones
- Dextromethadone
- Dipipanone
- Isomethadone=
- Levoisomethadone
- Levomethadone
- Methadone
- Methadone intermediate
- Normethadone
- Norpipanone
- Phenadoxone (heptazone)
Structures
| Amidones | ||||
|---|---|---|---|---|
|
|
|
 Levoisomethadone | |
 Noracetylmethadol |
 Levomethadone |
 Methadone |
 Methadone intermediate | |
 Normethadone |
 Norpipanone |
 Phenadoxone |
 Pipidone | |
Methadols
Structures
| Other open chain opioids | ||||
|---|---|---|---|---|
|
|
|
Noracetylmethadol | |
Moramides
Structures
| Other open chain opioids | ||||
|---|---|---|---|---|
|
|
|
|
|
Thiambutenes
Structures
Phenalkoxams
- Dextropropoxyphene (propoxyphene)
- Dimenoxadol
- Dioxaphetyl butyrate
- Levopropoxyphene
- Norpropoxyphene
- Pyrroliphene
Structures
| Phenalkoxams | ||||
|---|---|---|---|---|
Dextropropoxyphene |
|
|
|
|
Ampromides
Structures
| Ampromides | ||||
|---|---|---|---|---|
|
|
| ||
Others
Structures
| Other open chain opioids | ||||
|---|---|---|---|---|
|
|
|
|
|
Anilidopiperidines
- 3-Allylfentanyl
- 3-Methylfentanyl
- 3-Methylthiofentanyl
- 4-Phenylfentanyl
- Alfentanil
- α-Methylacetylfentanyl
- α-Methylfentanyl
- α-Methylthiofentanyl
- Benzylfentanyl
- β-hydroxyfentanyl
- β-hydroxythiofentanyl
- β-Methylfentanyl
- Brifentanil
- Butyrfentanyl
- Carfentanil
- Fentanyl
- Lofentanil
- N-Methylcarfentanil
- Mirfentanil
- Ocfentanil
- Ohmefentanyl
- Parafluorofentanyl
- Phenaridine
- R-30490
- Remifentanil
- Sufentanil
- Thenylfentanyl
- Thiofentanyl
- Trefentanil
Structures
Oripavine derivatives
Thienorphine
- 7-PET
- Acetorphine
- Alletorphine (N-allyl-noretorphine)
- BU-48
- Buprenorphine
- Buprenorphine-3-glucuronide
- Cyprenorphine
- Dihydroetorphine
- Etorphine
- Homprenorphine
- 18,19-Dehydrobuprenorphine (HS-599)
- N-cyclopropylmethylnoretorphine
- Nepenthone
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- Thevinone
- Thienorphine
Structures
| Oripavine derivatives | ||||
|---|---|---|---|---|
 7-PET |
 Acetorphine |
 Alletorphine |
 BU-48 |
 Buprenorphine |
 Cyprenorphine |
 Dihydroetorphine |
 Etorphine |
 Homprenorphine |
 18,19-Dehydrobuprenorphine |
 N-cyclopropylmethylnoretorphine |
 Nepenthone |
 Norbuprenorphine |
 Thevinone |
Thienorphine |
Phenazepanes
Structures
| Phenazepanes | ||||
|---|---|---|---|---|
|
|
|
|
|
Pirinitramides
Structures
| Pirinitramides | ||||
|---|---|---|---|---|
|
| |||
Benzimidazoles
Structures
| Benzimidazoles | ||||
|---|---|---|---|---|
|
|
|
|
|
Indoles
- 18-Methoxycoronaridine
- 7-Acetoxymitragynine
- 7-Hydroxymitragynine
- ψ-Akuammigine
- Akuammidine
- Akuammine
- Coronaridine
- Eseroline
- Hodgkinsine
- Ibogaine
- Mitragynine
- Mitragynine pseudoindoxyl
- Noribogaine
- Pericine
- Pseudoakuammigine
Structures
| Indoles | ||||
|---|---|---|---|---|
|
7-Acetoxymitragynine |
|
Akuammidine |
|
|
|
-Mitragynine_Structural_Formula_V1.svg.png.webp)
|
|
|
Beta-Amino Ketones
-2%252C2-dimethyl-1-phenylpropan-1-one.svg.png.webp)
Diphenylmethylpiperazines
Opioid peptides
Dynorphins
Structures
| Dynorphins | ||||
|---|---|---|---|---|
 Big dynorphin |
 Dynorphin A |
 Dynorphin B | ||
Endomorphins
Endorphins
Structures
Enkephalins
Structures
| Enkephalins | ||||
|---|---|---|---|---|
 DADLE |
 DAMGO |
 Deltorphin |
 Met-enkephalin |
 Leu-enkephalin |
Propeptides
Others / unknown
- Adrenorphin
- Amidorphin
- Biphalin
- Casokefamide
- Casomorphins
- Cytochrophin-4
- DALDA (Tyr-D-Arg-Phe-Lys-NH2)
- Deltorphin I
- Deltorphin II
- Deprolorphin
- Dermorphin
- DPDPE
- Frakefamide
- Gliadorphin
- Gluten exorphins
- Hemorphin-4
- Metkefamide
- Morphiceptin
- Nociceptin
- Octreotide
- Opiorphin
- Rubiscolin
- Soymorphins
- Spinorphin
- TRIMU 5
- Tynorphin
- Valorphin
- Zyklophin
Structures
| Other or unknown opioid peptides | ||||
|---|---|---|---|---|
 Adrenorphin |
 Amidorphin |
 Casomorphin |
 DALDA |
Deltorphin |
 Dermorphin |
 DPDPE |
 Endomorphin-1 Endomorphin-2 |
 Gliadorphin |
 Morphiceptin |
 Nociceptin |
 Octreotide |
 Opiorphin |
Rubiscolin |
 TRIMU 5 |
Others
- 3-(3-Methoxyphenyl)-3-ethoxycarbonyltropane
- AD-1211
- AH-7921
- Axomadol
- Azaprocin
- BDPC
- Bisnortilidine
- BRL-52537
- Bromadol
- Bromadoline
- Ciprefadol
- Ciramadol
- Doxpicomine
- Enadoline
- Faxeladol
- GR-89696
- Herkinorin
- ICI-199,441
- ICI-204,448
- Ketamine
- KNT-42
- LPK-26
- Lufuradom
- Metofoline
- MT-45
- Desmethylclozapine
- Nexeridine
- NNC 63-0532
- Nortilidine
- O-Desmethyltramadol
- Phenadone
- Phencyclidine
- Prodilidine
- Profadol
- Ro64-6198
- Salvinorin A
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- SB-612,111
- SC-17599
- RWJ-394,674
- TAN-67
- Tapentadol
- Thiobromadol (C-8813)
- Tifluadom
- Tilidine
- Tramadol
- Trimebutine
- U-47700
- U-50,488
- U-69,593
- Viminol
- 1-(4-Nitrophenylethyl)piperidylidene-2-(4-chlorophenyl)sulfonamide (W-18)
Opioid antagonists and inverse agonists
- 4-Caffeoyl-1,5-quinide
- 5'-Guanidinonaltrindole
- β-Funaltrexamine
- 6β-Naltrexol
- 6β-Naltrexol-d4
- Alvimopan
- AT-076
- Binaltorphimine
- BU09059
- Buprenorphine
- Chlornaltrexamine
- Clocinnamox
- Cyclazocine
- Cyprodime
- Diacetylnalorphine
- Diprenorphine (M5050)
- Fedotozine
- ICI-174864
- J-113,397
- JDTic
- JTC-801
- Levallorphan
- LY-2456302
- LY-255582
- Methocinnamox
- Methylnaltrexone
- ML350
- Naldemedine
- Nalfurafine
- Nalmefene
- Nalmexone
- Nalodeine (N-allylnorcodeine)
- Naloxazone
- Naloxegol
- Naloxol
- Naloxonazine
- Naloxone
- Naloxone benzoylhydrazone
- Nalorphine
- Naltrexone
- Naltriben
- Naltrindole
- Norbinaltorphimine
- Oxilorphan
- PF-4455242
- S-allyl-3-hydroxy-17-thioniamorphinan (SAHTM)
- Samidorphan
- SR-16430
Biased ligands
Receptor heteromer targeting ligands
Uncategorized opioids
- ADL-5859
- Alimadol
- Amentoflavone
- Anilopam +HCl
- Asimadoline
- Cyproterone acetate
- FE 200665
- Fedotozine
- HZ-2
- Kolokol-1
- Matrine
- MCOPPB
- Menthol
- MT-7716
- Nalfurafine
- Nalorphine
- Nalorphine dinicotinate
- PZM21
- Proglumide
- Ro65-6570
- SoRI-9409
- Spiradoline
- SR-8993
- SR-16435
Structures
| Uncategorized opioids | ||||
|---|---|---|---|---|
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|
 Nalodeine |
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Combination drug formulations containing opioids
- Buprenorphine/naloxone
- Buprenorphine/samidorphan (ALKS-5461)
- Co-codamol (codeine phosphate/paracetamol)
- Co-codaprin (codeine phosphate/aspirin)
- Co-dydramol (dihydrocodeine tartrate/paracetamol)
- Co-proxamol (dextropropoxyphene/paracetamol)
- Fentanyl/fluanisone
- Hydrocodone/ibuprofen
- Hydrocodone/paracetamol
- Loperamide/simethicone
- Morphine/naltrexone
- Naltrexone/bupropion
- Oxycodone/aspirin
- Oxycodone/naloxone
- Oxycodone/paracetamol
See also
References
- ↑ ChemIndex CAS Registry Number 3371-56-0
- ↑ ChemIndex CAS Registry Number 509-56-8
- ↑ ChemIndex CAS Registry Number 63715-94-6
- ↑ NCBI PubChem SID 750205
- ↑ chembase cbid_346222
- ↑ Gomes I, Fujita W, Gupta A, Saldanha SA, Saldanha AS, Negri A, Pinello CE, Eberhart C, Roberts E, Filizola M, Hodder P, Devi LA (2013). "Identification of a μ-δ opioid receptor heteromer-biased agonist with antinociceptive activity". Proc. Natl. Acad. Sci. U.S.A. 110 (29): 12072–7. Bibcode:2013PNAS..11012072G. doi:10.1073/pnas.1222044110. PMC 3718106. PMID 23818586.
- ↑ Yekkirala AS, Lunzer MM, McCurdy CR, Powers MD, Kalyuzhny AE, Roerig SC, Portoghese PS (2011). "N-naphthoyl-beta-naltrexamine (NNTA), a highly selective and potent activator of μ/kappa-opioid heteromers". Proc. Natl. Acad. Sci. U.S.A. 108 (12): 5098–103. Bibcode:2011PNAS..108.5098Y. doi:10.1073/pnas.1016277108. PMC 3064379. PMID 21385944.
External links
- Carbonate derivatives of 14β-hydroxycodeine "viz., 14β-hydroxy-6-O-(methoxycarbonyl)codeine, 6-O-methoxycarbonyl-14β-(methoxycarbonyloxy)codeine, and 14β-acetoxy-6-O-methoxy-carbonylcodeine, potential substrates for ring C modification in morphinane (sic) alkaloids, were synthesized for the first time." Russian Chemical Bulletin. August 2008, Volume 57, Issue 8, pp 1773–1774. Date: 11 Aug 2009; I. V. Evsikova, S. K. Moiseev, P. V. Petrovskii, V. N. Kalinin. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1739–1740
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