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베라트라민

Veratramine

HCID 6070
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
60-70-8
표준 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
분자식
C27H39NO2
평균 분자량
409.6 g/mol
단동위원소 질량
409.29807949

개요

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.

이름 및 식별자

우선 이름
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
현지명
베라트라민
영어명
veratramine
분자식
C27H39NO2
분자량
409.6

이름 및 동의어

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
이름 더 보기
베라트라민NSC 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

데이터베이스 식별자

CAS
60-70-8
PubChem CID
6070
DTXSID
DTXSID40871534
ChEMBL
CHEMBL464724
ChEBI
CHEBI:9951
UNII
RK363YG315
EC Number
683-091-5
Nikkaji
J4.805D

물성

구조 계산 물성

XLogP
4.3
극성 표면적
52.5 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
3
회전 가능 결합 수
2
무거운 원자 수
30
형식 전하
0
복잡도
676

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Plant Toxins
Color/Form · 2건

CRYSTALS

NEEDLES

Solubility · 2건

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

물리화학적 성질

녹는점
122 · 122-1240C
끓는 점
529.83 °C · 529.83°C (rough estimate)
밀도
1.0393 · 1.0393 (rough estimate)
굴절률
1.64 · 1.6400 (estimate)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
DMSO(최대 12mg/ml) 또는 에탄올(최대 10mg/ml)에 용해됩니다.
산도 계수 (pKa)
14.82 · 14.82±0.60(Predicted)
물리적 상태
고체
색상
갈색을 띤 노란색
Merck
14 · 14,9952
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChIKey
MALFODICFSIXPO-KFKQDBFTSA-N
SMILES
N1C[C@@H](C)C[C@@H](O)[C@@H]1[C@H](C1=C(C)C2C[C@@]3([H])[C@]([H])(C=2C=C1)CC=C1C[C@@H](O)CC[C@]31C)C

화학적 성질

White Solid

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazards Summary · 1건

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 · 1건

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%)

독성 정보

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 1건

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)

Natural Pollution Sources · 1건

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)...

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 5건

SIGNS OF POISONING WITH VERATRINE & RELATED ALKALOIDS ARE SALIVATION, PURGATION, VOMITING...DIURESIS, EXCITABILITY FOLLOWED BY PROSTRATION, WEAK & IRREGULAR PULSE, DEEP & SLOW RESPIRATIONS, & DEATH IN CONVULSIONS OR CONSEQUENT UPON PARALYSIS. /VERATRINE & RELATED ALKALOIDS/

IN MICE, VERATRAMINE PRODUCED A CHARACTERISTIC EXCITATORY ACTION ON THE CENTRAL NERVOUS SYSTEM, PRODUCING BOTH TREMOR AND A CHARACTERISTIC STRUGGLING BEHAVIOR. THIS BEHAVIORAL EXCITATION WAS ACCOMPANIED BY CHANGES IN SEROTONIN CONTENT IN HYPOTHALAMUS.

THE CHRONOTROPIC ACTION OF VERATRAMINE IN CULTURED RAT CARDIAC CELLS DID NOT APPEAR TO INVOLVE RECEPTOR MECHANISMS.

IN ANESTHETIZED VAGOTOMIZED DOGS, VERATRAMINE RESTORED HEART RATE AND LEFT VENTRICULAR PRESSURE TO CONTROL LEVELS AFTER GLUCAGON HAD SIGNIFICANTLY INCR BOTH PARAMETERS. HOWEVER, CONTINUATION OF THE GLUCAGON INFUSION AFTER VERATRAMINE LED TO A LIMITED BUT SIGNIFICANT INCR IN HEART RATE AND PRESSURE. ADDITIONAL EXPT INDICATED THAT VERATRAMINE BLOCKS THE CHRONOTROPIC, BUT NOT THE INOTROPIC, ACTION OF GLUCAGON.

For more Non-Human Toxicity Excerpts (Complete) data for VERATRAMINE (7 total), please visit the HSDB record page.

안전 데이터

rtecs
YX5094000
ridadr
UN 2811 6.1/PG III
HS 번호
2933.39.4100
포장분류
III
위험 등급
6.1
유해 물질 데이터
60-70-8(Hazardous Substances Data)

화학 및 산업

약리 정보

Mechanism of Action · 2건

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.

용도 및 제조

Uses · 2건

Secondary base in plants of the veratrum genus; [Merck Index]

Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum.

응용 분야 · 2건

개요This 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°.

용도The 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.

공급사100 곳

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추가 설명

정의ChEBI: A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.

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