Chemistry:Spiradoline

Spiradoline
Clinical data
Routes of; administration	N/A
ATC code	none;
Identifiers
	IUPAC name 2-(3,4-Dichlorophenyl)-N-methyl-N-[(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro[4.5]decan-8-yl] acetamide;
CAS Number	87151-85-7 ;
PubChem CID	55652;
IUPHAR/BPS	1653;
ChemSpider	50257 ;
UNII	N18ZH0M4NP;
ChEMBL	ChEMBL118865 ;
Chemical and physical data
Formula	C22H30Cl2N2O2
Molar mass	425.39 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC(=C(C=C4)Cl)Cl;
	InChI InChI=1S/C22H30Cl2N2O2/c1-25(21(27)14-16-5-6-17(23)18(24)13-16)19-7-9-22(8-4-12-28-22)15-20(19)26-10-2-3-11-26/h5-6,13,19-20H,2-4,7-12,14-15H2,1H3/t19-,20-,22-/m0/s1 ; Key:NYKCGQQJNVPOLU-ONTIZHBOSA-N ;
	(what is this?) (verify)

Short description: A κ-opioid agonist drug

Spiradoline (U-62066) is a drug which acts as a highly selective κ-opioid agonist.^[1] It has analgesic,^[2] diuretic,^[3] and antitussive effects,^[4] and produces subjective effects in animals similar to those of ketazocine and alazocine.^[5] The main effect in humans is sedation, along with analgesic and diuretic effects, but significant side effects such as dysphoria and hallucinations have stopped it from being used clinically.^[6]

References

↑ "Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid". The Journal of Pharmacology and Experimental Therapeutics 246 (1): 259–62. July 1988. PMID 2839665.
↑ "Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice". Life Sciences 45 (13): 1191–8. 1989. doi:10.1016/0024-3205(89)90508-0. PMID 2796604.
↑ "Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist". European Journal of Pharmacology 160 (2): 229–37. January 1989. doi:10.1016/0014-2999(89)90495-0. PMID 2547626.
↑ "Antitussive effects of two specific kappa-opioid agonists, U-50,488H and U-62,066E, in rats". European Journal of Pharmacology 187 (2): 281–6. October 1990. doi:10.1016/0014-2999(90)90014-w. PMID 2272363.
↑ "Further characterization of the discriminative stimulus effects of spiradoline". Pharmacology, Biochemistry, and Behavior 66 (3): 517–22. July 2000. doi:10.1016/s0091-3057(00)00172-6. PMID 10899364.
↑ "A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist". CNS Drug Reviews 9 (2): 187–98. 2003. doi:10.1111/j.1527-3458.2003.tb00248.x. PMID 12847558.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Spiradoline. Read more

[1] "Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid". The Journal of Pharmacology and Experimental Therapeutics 246 (1): 259–62. July 1988. PMID 2839665.

[2] "Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice". Life Sciences 45 (13): 1191–8. 1989. doi:10.1016/0024-3205(89)90508-0. PMID 2796604.

[3] "Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist". European Journal of Pharmacology 160 (2): 229–37. January 1989. doi:10.1016/0014-2999(89)90495-0. PMID 2547626.

[4] "Antitussive effects of two specific kappa-opioid agonists, U-50,488H and U-62,066E, in rats". European Journal of Pharmacology 187 (2): 281–6. October 1990. doi:10.1016/0014-2999(90)90014-w. PMID 2272363.

[5] "Further characterization of the discriminative stimulus effects of spiradoline". Pharmacology, Biochemistry, and Behavior 66 (3): 517–22. July 2000. doi:10.1016/s0091-3057(00)00172-6. PMID 10899364.

[6] "A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist". CNS Drug Reviews 9 (2): 187–98. 2003. doi:10.1111/j.1527-3458.2003.tb00248.x. PMID 12847558.

[1]

[2]

[3]

[4]

[5]

[6]

v t e Opioid receptor modulators
MOR	Agonists (abridged; see here for a full list): 3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 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 Lexanopadol Loperamide Loxicodegol Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine NalBzOH Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodine Nicomorphine NKTR-181 Norketamine Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol PAMs: BMS-986121 BMS-986122 Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan chloride Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Dihydroakuuamine Tabernanthine Tetrahydrocannabinol
DOR	Agonists: 3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine Antagonists: 4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
KOR	Agonists: 3CS-nalmefene 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuuamicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P 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 Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH 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) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-54,494A U-69,593 Xorphanol Antagonists: 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Aticaprant Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin UPHIT Zyklophin Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Dihydroakuuamine Ibogamine Tabernanthine
NOP	Agonists: (Arg14,Lys15)Nociceptin ((pF)Phe⁴)Nociceptin(1-13)NH₂ (Phe¹Ψ(CH₂-NH)Gly²)Nociceptin(1-13)NH₂ Ac-RYYRWK-NH₂ Ac-RYYRIK-NH₂ BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH₂ Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 TH-030418 Antagonists: (Nphe¹)Nociceptin(1-13)NH₂ AT-076 BAN-ORL-24 BTRX-246040 (LY-2940094) J-113,397 JTC-801 NalBzOH Nociceptin (1-7) Nocistatin SB-612,111 SR-16430 Thienorphine Trap-101 UFP-101
Unsorted	β-Casomorphins Amidorphin BAM-20P Cytochrophin-4 Deprolorphin Gliadorphin (gluteomorphin) Gluten exorphins Hemorphins Kava constituents MEAGL MEAP NEM Neoendorphins Nepetalactone (catnip) Peptide B Peptide E Peptide F Peptide I Rubiscolins Soymorphins
Others	Enkephalinase inhibitors: Amastatin BL-2401 Candoxatril D -Phenylalanine Dexecadotril (retorphan) Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Opiorphan Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Pronociceptin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
See also: Receptor/signaling modulators • Signaling peptide/protein receptor modulators

Anonymous

Search

Chemistry:Spiradoline

Namespaces

More

Page actions

See also

References

Navigation

Navigation

Help

Translate

Wiki tools

Wiki tools

Clinical data


Routes of administration	N/A
ATC code	none
Identifiers
IUPAC name 2-(3,4-Dichlorophenyl)-N-methyl-N-[(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro[4.5]decan-8-yl] acetamide
CAS Number	87151-85-7^Y
PubChem CID	55652
IUPHAR/BPS	1653
ChemSpider	50257^N
UNII	N18ZH0M4NP
ChEMBL	ChEMBL118865^N
Chemical and physical data
Formula	C₂₂H₃₀Cl₂N₂O₂
Molar mass	425.39 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC(=C(C=C4)Cl)Cl
InChI InChI=1S/C22H30Cl2N2O2/c1-25(21(27)14-16-5-6-17(23)18(24)13-16)19-7-9-22(8-4-12-28-22)15-20(19)26-10-2-3-11-26/h5-6,13,19-20H,2-4,7-12,14-15H2,1H3/t19-,20-,22-/m0/s1^N Key:NYKCGQQJNVPOLU-ONTIZHBOSA-N^N
^NY (what is this?) (verify)

Anonymous

Search

Chemistry:Spiradoline

See also

References

Navigation

Wiki tools

Page tools

Other projects

Categories