Phenazocine

Phenazocine
Clinical data
Other names	Fenazocina, Phenazocinum, DEA No. 9715
Routes of; administration	Oral
ATC code	N02AD02 (WHO) ;
Legal status
Legal status	AU: S9 (Prohibited substance) ; CA: Schedule I ; DE: Anlage I (Authorized scientific use only) ; UK: Class A Withdrawn; US: Schedule II ;
Identifiers
	show IUPAC name
CAS Number	58073-76-0 ;
PubChem CID	14707;
ChemSpider	391631 ;
UNII	J0ND6N0AQC;
ChEMBL	ChEMBL46399 ;
CompTox Dashboard (EPA)	DTXSID30110040 ;
ECHA InfoCard	100.004.397
Chemical and physical data
Formula	C22H27NO
Molar mass	321.464 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI
	(what is this?)

Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.^[1]

Effects of phenazocine include analgesia and euphoria, also may include dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors.^[2]

Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable μ/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an N-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics.^[3]

Consequently, phenazocine has four times the potency of morphine as an analgesic. Also it does not cause spasm of the sphincter of Oddi, making it more suitable than morphine for the treatment of biliary or pancreatic pain.^[4]

History[]

Phenazocine was invented in the 1950s.^[5]^[6] It was one of a number of benzomorphan opioids (including pentazocine, dezocine, and cyclazocine) developed in the search for non-addictive strong analgesics.

Phenazocine was once widely used, and was mainly supplied as 5 mg tablets of the hydrobromide salt for sublingual use (Narphen, Prinadol and other names), but its use was discontinued in the United Kingdom in 2001.^[7]

Phenazocine was briefly used in the United States but fell out of favor;^{[citation needed]} it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (Controlled Substances Act) of 1970 (CSA) but is not manufactured. The DEA ACSCN for phenazocine is 9715 and its 2013 annual manufacturing quota was 6 grams.^[8]

References[]

^ US 2959594, "Iso-benzmorphan derivatives"
^ Harris LS, Pierson AK (February 1964). "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics. 143: 141–8. PMID 14163985.
^ Feinberg AP, Creese I, Snyder SH (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences USA. 73 (11): 4215–9. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.
^ Hopton D. (January 1971). "Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain". Gut. 12 (1): 51–4. doi:10.1136/gut.12.1.51. PMC 1411461. PMID 4929685.
^ Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature. 184 (Suppl 7): 451. doi:10.1038/184451a0. PMID 13810504. S2CID 4190489.
^ Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology. 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222. S2CID 30670011.
^ "Monthly Release Terming and Coding Newsletter" (PDF). NHS Information Authority. February 2001. Archived from the original (PDF) on 2008-11-06. Retrieved 2008-01-11.
^ "Quotas - 2013". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

[1] US 2959594, "Iso-benzmorphan derivatives"

[Harris-2] Harris LS, Pierson AK (February 1964). "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics. 143: 141–8. PMID 14163985.

[Feinberg-3] Feinberg AP, Creese I, Snyder SH (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences USA. 73 (11): 4215–9. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.

[Hopton-4] Hopton D. (January 1971). "Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain". Gut. 12 (1): 51–4. doi:10.1136/gut.12.1.51. PMC 1411461. PMID 4929685.

[Clarke-5] Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature. 184 (Suppl 7): 451. doi:10.1038/184451a0. PMID 13810504. S2CID 4190489.

[Eckenhoff-6] Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology. 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222. S2CID 30670011.

[discontinueUK-7] "Monthly Release Terming and Coding Newsletter" (PDF). NHS Information Authority. February 2001. Archived from the original (PDF) on 2008-11-06. Retrieved 2008-01-11.

[8] "Quotas - 2013". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.

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show v t Opioid receptor modulators
MOR	Agonists (abridged; see here for a full list): 3-HO-PCP 7-Hydroxymitragynine α-Chlornaltrexamine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Alfentanil Anileridine Apparicine β-Endorphin Benzhydrocodone Benzylmorphine Bezitramide Biphalin Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Loperamide LS-115509 Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Nalmexone Naltalimide NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphone Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 U-47700 Valorphin Viminol Xorphanol PAMs: Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 4-Caffeoyl-1,5-quinide 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Hyperoside Ibogaine Levallorphan Lobeline LY-255582 Methylnaltrexone Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
DOR	Agonists: 6'-GNTI 7-SIOM Alazocine (SKF-10047) Amoxapine β-Endorphin Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 Ethylketazocine Etorphine Fentanyl Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SNC-80 TAN-67 (SB-205,607) Thebaine Thiobromadol (C-8813) Tonazocine Tramadol Xorphanol Zenazocine Antagonists: 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin LY-255582 Methylnaltrexone Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SoRI-9409 Taxifolin Thienorphine Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
KOR	Agonists: 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Alazocine (SKF-10047) Asimadoline Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lofentanil LPK-26 Lufuradom Matrine Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine Nalbuphine Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62,066) Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-69,593 Xorphanol Antagonists: 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone Apigenin AT-076 Aticaprant Axelopran Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox Dezocine EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2459989 Methylnaltrexone Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin Zyklophin Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Ibogamine Tabernanthine
NOP	Agonists: Buprenorphine Cebranopadol Dihydroetorphine Etorphine Levomethorphan Levorphanol MCOPPB NNC 63-0532 Nociceptin (orphanin FQ) Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 SR-16435 Antagonists: AT-076 BTRX-246040 (LY-2940094) J-113,397 JTC-801 SB-612,111 Thienorphine
Unsorted	β-Casomorphins Amidorphin Cytochrophin-4 Gliadorphin (gluteomorphin) Gluten exorphins Hemorphins Kava constituents NEM Neoendorphins Nepetalactone (catnip) Rubiscolins
Others	Enkephalinase inhibitors: Amastatin Candoxatril D -Phenylalanine Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

Clinical data

Other names	Fenazocina, Phenazocinum, DEA No. 9715
Routes of administration	Oral
ATC code	N02AD02 (WHO)
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A Withdrawn US: Schedule II
Identifiers
show IUPAC name (2R,6R,11R)-6,11-Dimethyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
CAS Number	58073-76-0^Y
PubChem CID	14707
ChemSpider	391631^N
UNII	J0ND6N0AQC
ChEMBL	ChEMBL46399^Y
CompTox Dashboard (EPA)	DTXSID30110040
ECHA InfoCard	100.004.397
Chemical and physical data
Formula	C₂₂H₂₇NO
Molar mass	321.464 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES C[C@H]1[C@H]2Cc3ccc(cc3[C@@]1(CCN2CCc4ccccc4)C)O
show InChI InChI=1S/C22H27NO/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17/h3-9,15-16,21,24H,10-14H2,1-2H3/t16-,21+,22+/m0/s1^N Key:ZQHYKVKNPWDQSL-KNXBSLHKSA-N^N
^NY (what is this?)

Phenazocine

History[]

See also[]

References[]