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Veratramine

Veratramine structure

CAS No:
60-70-8
Formula:
C27H39NO2
Chemical Name:
Veratramine
Synonyms:
3-Piperidinol,5-methyl-2-[(1S)-1-[(3S,6aR,11aS,11bR)-2,3,4,6,6a,11,11a,11b-octahydro-3-hydroxy-10,11b-dimethyl-1H-benzo[a]fluoren-9-yl]ethyl]-,(2S,3R,5S)-;Veratramine;Veratraman-3,23-diol,14,15,16,17-tetradehydro-,(3β,23β)-;1H-Benzo[a]fluorene,veratraman-3,23-diol deriv.;(2S,3R,5S)-5-Methyl-2-[(1S)-1-[(3S,6aR,11aS,11bR)-2,3,4,6,6a,11,11a,11b-octahydro-3-hydroxy-10,11b-dimethyl-1H-benzo[a]fluoren-9-yl]ethyl]-3-piperidinol;NSC 17821;NSC 23880;10159-78-1
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.

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.

Veratramine Basic Attributes

Molecular Weight：

409.614

Exact Mass：

409.60

UNII：

RK363YG315

NSC Number：

17821|23880

Color/Form：

CRYSTALS|NEEDLES

Characteristics

PSA：

52.5

XLogP3：

4.3

Density：

1.1±0.1 g/cm3

Melting Point：

206 °C

Boiling Point：

565°C at 760 mmHg

Flash Point：

86.2±20.7 °C

Refractive Index：

1.601

Water Solubility：

SOL IN BENZENE, CHLOROFORM, DIL ACID; INSOL IN DIL ALKALI

Specific rotation：

SPECIFIC OPTICAL ROTATION: -71.8 DEG @ 25 °C/D (WATER 1.21%), -70 DEG @ 25 °C/D (METHANOL 1.56%); MAX ABSORPTION: 268 NM

Experimental Properties：

PRECIPITATED BY DIGITONIN

Safety Information

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)]

GHS Classification：

|Warning|H302 (95%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Natural Pollution Sources：

SECONDARY BASE FROM VERATRUM GRANDIFLORUM (MAXIM) LOES F, & FROM V VIRIDE AIT, LILIACEAE. ISOLATION & STRUCTURE: SAITO, BULL CHEM SOC JAPAN 15, 22 (1940); JACOBS, CRAIG, J BIOL CHEM 160, 555 (1945)...TOTAL SYNTHESIS: MASAMUNE ET AL, J AM CHEM SOC 89, 4521 (1967)...

Drug Information

Reported Fatal Dose：

3 OR 4. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /VERATRUM VIRIDE ALKALOIDS/

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.

MeSH Entry Terms：

5-methyl-2-(1-(2,3,4,6,6a,11,11a,11b-octahydro- 3-hydroxy-10,11b-dimethyl-1H-benzo(a)fluoren-9- yl)ethyl)piperidin-3-ol

Veratramine Use and Manufacturing

It is useful as signal transduction inhibitor for treating tumors The hedgehog (Hh) signaling pathway, which is blocked by cyclopamine , plays a key role in morphogenesis and has potential applications in the treatment of cancer. Veratramine, a teratogenic steroidal alkaloid isolated from the corn lily (Veratrum sp.), is an analog of cyclopamine that can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM. Additionally, veratramine has anti-thrombotic activity as it dose dependently inhibits platelet aggregation in rabbits ex vivo. While it may be most useful as a signal transduction inhibitor for treating tumors, veratramine also induces serotonin release and inhibits its re-uptake in the CNS.

Computed Properties

Molecular Weight:409.6
XLogP3:4.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:409.298079487
Monoisotopic Mass:409.298079487
Topological Polar Surface Area:52.5
Heavy Atom Count:30
Complexity:676
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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