Chlornaltrexamine: Information from Answers.com

Chlornaltrexamine

IUPAC name	6-(Bis(2-chloroethyl)amino)- 17-(cyclopropylmethyl)- 4,5-epoxy- (5-alpha,6-beta)- morphinan- 3,14-diol
Other names	alpha-chlornaltrexamine
Identifiers
CAS number	67025-94-9
PubChem	5486190
SMILES	`O[C@@]13[C@]2([C@@H]5[C@H](N(CCCl)CCCl)CC3)C4=C(C=CC(O)=C4O5)C[C@H]1N(CC6CC6)CC2`
Properties
Molecular formula	C₂₄H₃₂Cl₂N₂O₃
Molar mass	467.43 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chlornaltrexamine is an irreversible mixed agonist-antagonist for μ-opioid receptors, which forms a covalent bond to the active site. It is 22 times more potent than morphine. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the nitrogen mustards.^[1]

References

^ L. M. Sayre; A. E. Takemori; P. S. Portoghese (1983). Journal of Medicinal Chemistry 26 (4): 503. doi:10.1021/jm00358a009.

Opioids (N02A)

Opium
derivatives

Whole Opium
Preparations

Compote/Kompot/Polish Heroin • Diascordium • B & O Supprettes • Dover's powder • Laudanum • Mithridate • Opium • Paregoric • Concentrate of Poppy Straw (CPS) • 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	14-Hydroxymorphine • 14β-Hydroxymorphine • 14β-Hydroxymorphone • 2,4-Dinitrophenylmorphine • 6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 6-Acetyldihydromorphine/6-Monoacetyldihydromorphine • Acetyldihydromorphine • Azidomorphine • Chlornaltrexamine • Chloromorphide • Dihydrodesoxymorphine (Desomorphine) • Dihydromorphine • Ethyldihydromorphine • Hydromorphinol • Methyldesorphine • N-Phenethylnormorphine • Pseudomorphine

3,6 Diesters of Morphine	Diacetyldihydromorphine (Dihydroheroin) • Dibenzoylmorphine • Dibutanoylmorphine • Dipropanoylmorphine • Disalicyloylmorphine • Heroin (Diacetylmorphine) • Heroin-7,8-Oxide • Nicomorphine

Codeine-Dionine Family	14-Hydroxydihydrocodeine • Acetylcodeine • Benzylmorphine • Codeine methylbromide • Desocodeine • Methyldihydromorphine (Dihydroheterocodeine) • Ethylmorphine (Dionine) • Heterocodeine • Isocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine • Nalodeine • Transisocodeine

Morphinones	14-Ethoxymetopon • 14-Methoxymetopon • 14β-Hydroxymorphone • 14-O-Methyloxymorphone • 14-phenylpropoxy-5-methyl-hydromorphone • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • 8,14-Dihydroxydihydromorphinone • Acetylmorphone • Ethyldihydromorphinone • Hydromorphinone • Hydromorphone • Hydroxycodeine • Methyldihydromorphinone • Metopon • Morphinol • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone

Codeinones	1-carboxy-14-hydroxydihydrocodeinone • 1-carbethoxy-14-hydroxydihydrocodeinone • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Codeinone • Codorphone • Codoxime • Hydrocodone • Monodihydrocodeineone • Oxycodone

Dihydrocodeine Series	14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Dihydrodesoxycodeine/Desocodeine • Dihydroisocodeine • Nicocodeine • Nicodicodeine

Nitrogen Morphine Derivatives	Codeine-N-Oxide • Heroin-N-Oxide • Hydromorphone-N-Oxide • Morphine-N-Oxide

Hydrazones	Hydromorphazone • Morphazone • Oxymorphazone

Others	α-chlorocodide • Pholcodine

Active Opiate
Metabolites

Codeine-N-Oxide (Genocodeine) • Hydromorphone-N-Oxide • Heroin-7,8-Oxide • Morphine-3-glucuronide • Morphine-6-glucuronide • Monoacetylmorphine • Morphine-N-Oxide (Genomorphine) • Naltrexol • Norcodeine • Normorphine

Morphinans

Morphinan Series	4-chlorophenylpyridomorphinan • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • 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)	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 • Levomethadyl acetate (Acetylmethadol) • 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 • 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

Phenazepines

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

Azaprocin • BDPC • Bisnortilidine • BRL-52537 • C-8813 • Ciramadol • Enadoline • Faxeladol • Herkinorin • J-113,397 • JTC-801 • Methopholine • 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 • 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)

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Chlornaltrexamine

See also

References