Veratramine
Grundinformationen
- CAS
60-70-8- Standard-SMILES
Cc1c([C@H](C)[C@@H]2NC[C@@H](C)C[C@H]2O)ccc2c1C[C@H]1[C@H]2CC=C2C[C@@H](O)CC[C@@]21C- InChIKey
MALFODICFSIXPO-KFKQDBFTSA-N- Summenformel
- C27H39NO2
- Durchschnittliche Molmasse
- 409,6 g/mol
- Monoisotopische Masse
- 409,29807949
Überblick
Veratramine is a piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions. It derives from a hydride of a veratraman.
Namen und Bezeichner
- Bevorzugter Name
- Veratramine
- IUPAC
- (2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol
- Englischer Name
- veratramine
- Summenformel
- C27H39NO2
- Molmasse
- 409.6
Namen und Synonyme
VERATRAMINE60-70-8(3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diolRK363YG315NSC-17821NSC-23880CHEBI:9951DTXSID40871534(3beta,23R)-14,15,16,17-tetradehydroveratraman-3,23-diolVeratraman-3,23-diol, 14,15,16,17-tetradehydro-, (3beta,23beta)-RefChem:193959DTXCID501474790
Weitere Namen anzeigen
NSC 2388AIDS011940veratraMinVeratramine(P)Veratramine-RMVeratramine, >99%
(3 beta,23 beta)-14,15,16,17-tetradehydroveratraman-3,23-diol(2S,3R,5S)-2-((1S)-1-((1S,2R,5S,10R)-5-hydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,16)heptadeca-7,11(16),12,14-tetraen-14-yl)ethyl)-5-methylpiperidin-3-olNSC 17821NSC 23880VreaframineNSC17821NSC23880MFCD00468124
Datenbank-Bezeichner
- CAS
60-70-8- PubChem CID
- 6070
- DTXSID
DTXSID40871534
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,3
- Polarare Oberfläche (TPSA)
- 52,5 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 676
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Plant Toxins
Color/Form
CRYSTALS
NEEDLES
Solubility
SLIGHTLY SOL IN WATER; SOL IN METHANOL, ALC
SOL IN BENZENE, CHLOROFORM, DIL ACID; INSOL IN DIL ALKALI
Melting PointMP: 209.5-210.5 °C /HYDRATE/
Optical RotationSPECIFIC OPTICAL ROTATION: -71.8 DEG @ 25 °C/D (WATER 1.21%), -70 DEG @ 25 °C/D (METHANOL 1.56%); MAX ABSORPTION: 268 NM
Physical DescriptionSolid; [Merck Index]
Other Experimental PropertiesPRECIPITATED BY DIGITONIN
Physikochemische Eigenschaften
- Schmelzpunkt
- 122 · 122-1240C
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (90.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazards Summary
Emergency treatment: Plants- veratrum alkaloids; Excessive amounts can cause death by central respiratory depression; [HSDB] Veratrum alkaloids (e.g., black snakeroot, false hellebore, and skunk cabbage) cause gastroenteritis, bradycardia, paresthesias, AV block, and syncope;; [Olson, p. 376-92]
Special Reports
A REVIEW WITH MANY REF OF VERATRAMIN AND ITS ABILITY TO ANTAGONIZE SELECTIVELY THE POS CHRONOTROPIC ACTION OF SYMPATHOMIMETIC AMINES AND OTHER SUBSTANCES.[KRAYER O; ON THE ANTIACCELERATOR ACTIVITY OF VERATRAMINE WITH SOME REMINISCENCES ON THE ANTECEDENTS OF ITS DISCOVERY; DOSTIZH SOVREM FARMAKOL 59-70 (1976)]
Hazard Classes and CategoriesAcute Tox. 4 (90.5%)
Toxikologische Informationen
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary
Veratramine produces a characteristic excitatory action on the central nervous system, producing both tremor and a characteristic "struggling" behavior. This behavioral excitation is accompanied by changes in serotonin content in hypothalamus. The central serotonin agonist methysergide in doses of 5--15 mg per kg produces a dose-dependent inhibition of veratramine's action, while parachlorophenylalanine has no effect. (A15440)
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
THE EFFECTS OF VERATRAMINE ON TRANSMEMBRANE POTENTIALS OF THE ISOLATED RIGHT ATRIAL PREPN OF THE CAT WERE EXAMINED. VERATRAMINE SLOWED THE SPONTANEOUS RATE & PPTD A CHARACTERISTIC RHYTHM CONSISTING OF ALTERNATING PERIODS OF ASYSTOLE & NORMAL ATRIAL RHYTHM (PERIODIC RHYTHM). AFTER LARGE DOSES OR CONTINUED EXPOSURE TO LOW DOSES OF VERATRAMINE, ELECTRICAL & MECHANICAL ACTIVITY OF THE ATRIA CEASED; SUBSEQUENTLY ACTIVITY RESUMED ONLY IN A DISCRETE AREA WITHIN WHICH ACTION POTENTIALS WERE CONSISTENT WITH PACEMAKER CHARACTERISTICS.
L-ETHOMOXANE HYDROCHLORIDE CAUSED 1/30TH & BETWEEN 1/10 & 1/20TH OF THE NEGATIVE CHRONOTROPIC EFFECT INDUCED BY VERATRAMINE ON THE DOG HEART-LUNG PREPN & ON THE ISOLATED GUINEA PIG ATRIUM, RESPECTIVELY.
Verwendung und Herstellung
Uses
Secondary base in plants of the veratrum genus; [Merck Index]
Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum.
Anwendungen
BeschreibungThis alkaloid occurs naturally in Veratrum grandi/lorum and V. viride and is also formed during the hydrolysis of Veratrosine (q.v.). It forms colourless crystals of the monohydrate from aqueous EtOH and has [α]19D - 70° (MeOH). The hydrochloride forms colourless plates from EtOH, m.p. 20l-2°C and the picrate, yellow plates, m.p. 217.5 - 218°C. Two non-phenolic hydroxyl groups and an imino group are present and the triacetyl derivative, m.p. 205.5-206°C; [α]14.5D + 37.8° (MeOH), on controlled hydrolysis furnishes the N-acetyl com_x0002_pound, m.p. 176-8°C. The O-acetate has also been prepared as colourless prisms from aqueous EtOH, m.p. 20l-2°C but it is still uncertain which of the hydroxyl groups is acetylated in this derivative. Treatment with methyl iodide in MeOH in the presence of sodium carbonate gives N-methylveratraminc methiodide, m.p. 268°C (dec.) from which the methochloride, m.p. 277°C can be obtained. On catalytic hydrogenation, the base furnishes the dihydro derivative, m.p. 198- 200°C; [α]27D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]28D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]24D + 84°.
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