Rhynchophylline

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Rhynchophylline
Systematic (IUPAC) name

methyl (7β,16E,20α)-16-(methoxymethylene)- 2-oxocorynoxan- 17-oate
Identifiers
CAS number	76-66-4
ATC code	none
PubChem	3033948
Chemical data
Formula	C₂₂H₂₈N₂O₄
Mol. mass	384.46872 g/mol
SMILES	eMolecules & PubChem
Synonyms	methyl (E)-2-[(3R,6'R,7'S,8'aS)- 6'-ethyl- 2-oxospiro[1H-indole-3,1'- 3,5,6,7,8,8a-hexahydro- 2H-indolizine]- 7'-yl]- 3-methoxyprop- 2-enoate
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Rhynchophylline is an alkaloid found in certain Uncaria species, notably Uncaria rhynchophylla^[1] and Uncaria tomentosa.^[2] It is a non-competitive NMDA antagonist and calcium channel blocker^[3]^[4]

References

^ Shi JS, Yu JX, Chen XP, Xu RX. Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline. Acta Pharmacologica Sinica. 2003 Feb;24(2):97-101. PMID 12546715
^ Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H. Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test. Journal of Pharmacy and Pharmacology. 2000 Dec;52(12):1553-61. PMID 11197086
^ Kang TH, Murakami Y, Matsumoto K, Takayama H, Kitajima M, Aimi N, Watanabe H.Rhynchophylline and isorhynchophylline inhibit NMDA receptors expressed in Xenopus oocytes. Eur J Pharmacol. 2002 Nov 22;455(1):27-34.
^ Kang TH, Murakami Y, Takayama H, Kitajima M, Aimi N, Watanabe H, Matsumoto K. Protective effect of rhynchophylline and isorhynchophylline on in vitro ischemia-induced neuronal damage in the hippocampus: putative neurotransmitter receptors involved in their action. Life Sci. 2004 Dec 3;76(3):331-43.

Glutamatergics

Ionotropic

AMPA	Agonists: 5-Fluorowillardiine • AMPA • Domoic Acid • Quisqualic Acid; Positive Allosteric Modulators: Aniracetam • Cyclothiazide • CX-516 • CX-546 • CX-614 • CX-691 • CX-717 • IDRA-21 • LY-392,098 • LY-404,187 • LY-451,395 • LY-451,646 • LY-503,430 • Oxiracetam • PEPA • Piracetam • Pramiracetam • Sunifiram • Unifiram Antagonists: ATPO • Caroverine • CNQX • DNQX • GYKI-52466 • NBQX • Perampanel • Tezampanel (LY-293,558); Negative Allosteric Modulators: GYKI-53,655
NMDA	Agonists: Glutamate/Acite Site Competitive Agonists: Aspartate • Glutamate • Homoquinolinic Acid • Ibotenic Acid • NMDA • Quinolinic Acid • Tetrazolylglycine; Glycine Site Agonists: ACBD • ACPC • ACPD • Alanine • CCG • Cycloserine • DHPG • Fluoroalanine • Glycine • HA-966 • L-687,414 • Milacemide • Sarcosine • Serine • Tetrazolylglycine; Polyamine Site Agonists: Acamprosate • Spermidine • Spermine Antagonists: Competitive Antagonists: AP5 (APV) • AP7 • CGP-37849 • CGP-39551 • CGP-39653 • CGP-40116 • CGS-19755 • CPP • LY-233,053 • LY-235,959 • LY-274,614 • MDL-100,453 • Midafotel (d-CPPene) • NPC-12,626 • NPC-17,742 • PBPD • PEAQX • Perzinfotel • PPDA • SDZ-220581 • Selfotel (CGS-19,755); Noncompetitive Antagonists: ARR-15,896 • Caroverine • Dexanabinol (HU-211) • FPL-12495 • FR-115,427 • Hodgkinsine • Magnesium • MDL-27,266 • NPS-1506 • Psychotridine • Zinc; Uncompetitive Pore Blockers: 2-MDP • 8A-PDHQ • Amantadine • Aptiganel (CNS-1102) • ARL-12,495 • ARL-15,896-AR • ARL-16,247 • Budipine • Delucemine • Dexoxadrol • Dieticyclidine • Dizocilpine (MK-801) • Endopsychosin • Esketamine • Etoxadrol • Eticyclidine • Gacyclidine • Ibogaine • Indantadol (CHF-3381) • Ketamine • Ketobemidone • Loperamide • Memantine • Meperidine (Pethidine) • Methadone • Methorphan (Dextromethorphan, Levomethorphan) • Milnacipran • Morphanol (Dextrorphan, Levorphanol) • NEFA • Neramexane • Nitrous Oxide • Noribogaine • Orphenadrine • Phencyclamine • Phencyclidine • Propoxyphene • Remacemide • Rhynchophylline • Riluzole • Rimantadine • Rolicyclidine • Tenocyclidine • Tiletamine • Tramadol • Xenon; Glycine Site Antagonists: ACEA-1021 • ACEA-1328 • ACPC • Carisoprodol • CGP-39653 • CKA • DCKA • Felbamate • Gavestinel (GV-150,526) • GV-196,771 • Kynurenic Acid • L-689,560 • L-701,324 • Lacosamide • Licostinel (ACEA-1021) • LU-73,068 • MDL-105,519 • Meprobamate • MRZ 2/576 • PNQX • ZD-9379; NR2B Subunit Antagonists: Besonprodil • CO-101,244 (PD-174,494) • CP-101,606 • Eliprodil • Haloperidol • Ifenprodil • Isoxsuprine • Nylidrin • Ro8-4304 • Ro25-6981 • Traxoprodil; Polyamine Site Antagonists: Arcaine • Co 101676 • Diaminopropane • Diethylenetriamine • Huperzine A • Putrescine • Ro 25-6981; Unclassified/Unsorted Antagonists: Chloroform • Diethyl Ether • Enflurane • Ethanol (Alcohol) • Halothane • Isoflurane • Methoxyflurane
Kainate	Agonists: 5-Iodowillardiine • ATPA • Domoic Acid • Kainate • LY-339,434 • SYM-2081 Antagonists: CNQX • DNQX • LY-382,884 • NBQX • NS102 • UBP-302; Negative Allosteric Modulators: NS-3763

Metabotropic

Group I	Agonists: Unselective: ACPD • DHPG • Quisqualic Acid; mGlu1-Selective: Ro01-6128 • Ro67-4853 • Ro67-7476 • VU-71; mGlu5-Selective: ADX-47273 • CDPPB • CHPG • DFB • VU-1545 Antagonists: Unselective: MCPG • NPS-2390; mGlu1-Selective: BAY 36-7620 • CPCCOEt • LY-367,385 • LY-456,236; mGlu5-Selective: DMeOB • Fenobam • LY-344,545 • MPEP • MTEP • SIB-1757 • SIB-1893
Group II	Agonists: Unselective: CBiPES • DCG-IV • Eglumegad (LY-354,740) • LY-379,268 • LY-404,039 • LY-487,379 • MGS-0028; mGlu2-Selective: BINA • LY-566,332 Antagonists: Unselective: APICA • EGLU • HYDIA • LY-307,452 • LY-341,495 • MCPG: mGlu2-Selective: PCCG-4; mGlu3-Selective: CECXG
Group III	Agonists: Unselective: L-AP4; mGlu4-Selective: PHCCC • VU-001,171 • VU-0155,041; mGlu7-Selective: AMN082; mGlu8-Selective: DCPG Antagonists: Unselective: CPPG • MAP4 • MSOP • MPPG • MTPG • UBP-1112; mGlu7-Selective: MMPIP

Transporter
Inhibitors

EAATs	DHKA • PDC • WAY-213,613
vGluTs	7-CKA • Evans Blue
TRPC6	Adhyperforin • Hyperforin

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Arabic	Bulgarian	Chinese	Czech
Danish	Dutch	English	Estonian
Finnish	French	German	Greek
Hungarian	Italian	Japanese	Korean
Norwegian	Polish	Portuguese	Romanian
Russian	Serbian	Slovenian	Spanish
Swedish	Turkish	Latvian	Persian
Lithuanian	Icelandic	Slovak	Croatian
Hindi	Vietnamese	Hebrew	Thai
Indonesian