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ERGOTAMINE TARTRATE

CAS No.
379-79-3
Chemical Name:
ERGOTAMINE TARTRATE
Synonyms
ergomar;ergostat;etin;ergam;ergate;exmigra;lingran;secagyn;secupan;femergin
CBNumber:
CB9279489
Molecular Formula:
C70H76N10O16
Molecular Weight:
1313.41
MDL Number:
MFCD08277639
MOL File:
379-79-3.mol
Modify Date:2022-08-15 17:40:09

ERGOTAMINE TARTRATE Properties

Melting point ~195 °C (dec.)(lit.)
alpha D25 -125 to -155° (c = 0.4 in chloroform)
storage temp. 2-8°C
Merck 13,3696
BRN 6173437
CAS DataBase Reference 379-79-3(CAS DataBase Reference)
EWG's Food Scores 2
FDA UNII MRU5XH3B48
Proposition 65 List Ergotamine Tartrate
EPA Substance Registry System Ergotamine tartrate (379-79-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H301+H311+H331-H361
Precautionary statements  P261-P280-P301+P330+P331+P310-P302+P352+P312-P304+P340+P311-P403+P233
Hazard Codes  T
Risk Statements  23/24/25-62-63
Safety Statements  36/37-45
RIDADR  UN 1544 6.1/PG 1
WGK Germany  3
RTECS  KE8225000
3-8-10
HazardClass  6.1(b)
PackingGroup  III
HS Code  29396200

ERGOTAMINE TARTRATE price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1241506 Ergotamine tartrate 379-79-3 150mg $448 2022-05-15 Buy
Chem-Impex 41611 ErgotamineD-tartrate,≥97% ≥97% 379-79-3 10G $160.74 2021-12-16 Buy
Product number Packaging Price Buy
1241506 150mg $448 Buy
41611 10G $160.74 Buy

ERGOTAMINE TARTRATE Chemical Properties,Uses,Production

Description

Ergotamine and ergometrine belong to two kinds of ergot alkaloids. Ergot (Claviceps purpurea, 麦角) is the sclerotium of ergot fungus that grows in the rye and related cereal and forage plants. The ergot is grown in the northeast and north China and Xinjiang, Jiangsu, Zhejiang, Sichuan, and other places. At present, the method of growth of ergot is inoculation cultivation.
Traditional Chinese medicine believes that ergot is tasteless, tepid, toxic, liver meridian, and kidney meridian. The traditional usage of ergot is oral administration of extractum, 2–4 ml each time, daily amount of 6–8 ml. Its dosage forms also contain infusion, pills, injection, etc. Pharmacology of Chinese Medicine records ergot can be used for uterine contraction, uterine bleeding, and postpartum hemorrhage after delivery, incomplete recovery of uterus, retrogression, etc. The Plateau Chinese herbal medicine treatment manual records that ergot can cure migraine.

Chemical Properties

White Solid

Chemical Properties

Ergotamine tartrate is a crystalline solid.

Physical properties

Appearance: White or slightly yellow fine crystalline powder with slight hygroscopicity. Solubility: Slightly soluble in water and ethanol, insoluble in ether and chloroform.

History

As a kind of traditional Chinese medicine, ergot was originally used for hemostasis and involution of uterus by stimulating the uterine muscle powerfully and persistently. After the modernization the traditional Chinese medicine was putting forward, by making several kinds of wild ergot into extractum, we found that all of them can promote the contraction of the rabbit uterus in vivo and in vitro. In isolated rabbit uterus, the effect of ergot on postpartum uterus and pregnant uterus was stronger than nonpregnant uterus. Among a variety of active ingredients in the ergot, ergonovine has the strongest effect on uterine, followed by ergotamine. Seventeen of the 131 strains of ergot derived from the host plants of our country are able to produce ergot alkaloids in wheat culture medium. Among the strains, Claviceps microcephala Ce-3 produces the most ergonovine. Therefore, it became the main bacteria used in the process of industrialization. The study suggested that ergotamine or ergot can block the a-adrenergic receptor, so that the pressor effect of adrenaline was reversed. They do not prevent the release of sympathetic mediators. It showed that the effect of ergotamine is similar to norepinephrine on the hypogastric nerve of guinea pig in vitro. Low dose of ergot can stimulate the brain (slow heart rate, breathing, convulsions, etc.) whereas high dose can cause deaths due to the delayed paralysis. In addition, it can enhance the sedative and hypnotic effects of barbiturates, morphine, and methadone.

Uses

diuretic, inhibits Na/K/2Cl carrier system

Uses

Antimigraine.

Indications

Ergometrine maleate is used in the form of extract tumor injection. As a uterotonic, ergometrine maleate is mainly used for the prevention and treatment of uterine bleeding caused by weak or poor uterine contraction after delivery or abortion, as well as the incomplete recovery of postpartum uterus to accelerate the recovery of uterus.
Ergotamine tartrate is used for the treatment of migraine in the form of tablet and parenteral solution. It also can be used for other neurogenic headache as well.

brand name

Ergomar (Harvest);Ergostat (Parke-Davis); Wigrettes (Organon).

General Description

Powder or liquid forms available as drugs. Used in obstetrics and in the treatment of migraine headaches.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

ERGOTAMINE TARTRATE is sensitive to prolonged exposure to heat and light. . When heated to decomposition, ERGOTAMINE TARTRATE emits toxic fumes of nitrogen oxides. Protect from light and heat [EPA, 1998].

Health Hazard

High oral toxicity and a convulsant in humans.People with liver damage are at a greater risk.

Fire Hazard

When heated to decomposition, ERGOTAMINE TARTRATE emits toxic fumes of nitrogen oxides. Protect from light and heat

Pharmacology

1. The effect of uterus excitation
The effect of ergot on the uterine muscle is similar to the posterior pituitary preparation, which directly acts on the uterine muscle with more powerful and lasting effects. The pregnant uterus is more sensitive to ergot. Low dose of ergot has significant effects on the uterus of labor and new postpartum with severely tetanic contraction. The extracts from several kinds of wild ergot can promote the contraction and increase the tension of uterus in rabbit in vivo and in vitro . Among a variety of active ingredients in the ergot, ergonovine has the strongest effect on uterus, followed by ergotamine.
2. The effects on cardiovascular
In the isolated vascular experiment, ergotamine can cause the contraction of peripheral vascular smooth muscle and hypertension due to vasoconstriction and boost and eventually produce compensatory bradycardia. Ergot has less effect on the heart than blood vessels, but when the heart rate drops to a certain extent, it can enhance the cardiac contractility. High dose of ergotamine can damage vascular endothelial cells (the mechanism is unknown), leading to gangrene. Ergotine has the strongest effect on blood vessels, and ergometrine hardly affects blood pressure and damages to vascular endothelial cells. Ergotine can cause vasoconstriction and decrease the arterial pulse amplitude, which may be related to the therapeutic effect on migraine.
3. The effects on the nervous system
Ergotamine or ergot can block the a-adrenergic receptor and reverse the pressor effect of adrenaline without preventing the release of sympathetic neurotransmitters. Low dose of ergot stimulates the brain (slow down heart rate, breathing, convulsions, etc.), whereas high dose causes deaths due to the delayed paralysis. Ergotamine enhances the sedative and hypnotic effects of barbiturates, morphine, and methadone.

Clinical Use

Ergonovine maleate is mainly used for the prevention and treatment of the weak uterine contraction or poor contraction caused by uterine bleeding after delivery or abortion. It is also used for incomplete recovery of postpartum uterus to accelerate the recovery of the uterus.
Ergotamine tartrate is mainly used for the treatment of migraine by relieving the symptoms. However, it is only suitable for short-term usage of headache attacks, normally does not prevent migraine. The combination of ergotamine tartrate and caffeine is better than single oral administration with the mild side effects. It also can be used for other neurogenic headaches.

Safety Profile

Poison by ingestion, intravenous, and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: hallucinations, dstorted perceptions, convulsions, nausea or vomiting, blood pressure elevation. Experimental reproductive effects. Human mutation data reported. Used in production of drugs of abuse. When heated to decomposition it emits toxic fumes of NOx. See also ERGOT.

Potential Exposure

(Toxicity evaluation); Suspected reprotoxic hazard, Suspected of causing genetic defects. The major uses of the ergot alkaloids fall into two categories: applications in obstetrics and treatment of migraine headaches. May be used in the production of “street” drugs

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Purification Methods

It crystallises from MeOH. [Beilstein 25 III/IV 964.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, light, and heat

ERGOTAMINE TARTRATE Preparation Products And Raw materials

Raw materials

Preparation Products

(5α)-12'-Hydroxy-2'-Methyl-5'-(phenylMethyl)-ergotaMan-3',6',18-trione (2R,3R)-2,3-Dihydroxybutanedioate ergotaMine tertrate dihydrate L-Ascorbic acid,L-Threoascorbic acid, Antiscorbutic factor, VitaminC ERGOTAMINE TARTRATE (ERGOT ALKALOIDW/BRO AD RANGE OF PHYS ERGOTAMIN D-TARTRAT 97% Ergotamine Tartrate (150 mg) (List Chemical) -,[theta-(theta,theta)]-2,3-dihydroxybutanedioate(2:1)(salt) 6’,18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-ergotaman-3(5’alpha) ergam ergate ergotaminebitartrate ergotartrate etin exmigra femergin gotaminetartrate gynergen lingraine lingran neo-ergotin rigetamin secagyn secupan ERGOTAMINE TARTRATE ERGOTAMINE D-TARTRATE, PH EUR Ergotaman-3,6,18-trione, 12-hydroxy-2-methyl-5-(phenylmethyl)-, (5.alpha.)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt) ERGOTAMINETARTRATE(CONTROLLEDCHEMICAL) ERGOTAMINETARTRATE,USP 8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine, ergotaman-3',6',18-trione deriv. Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'a)-, [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:1) (salt) Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'α)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1) (salt) Ergotamine tartrate (7CI) Ergotamine, tartrate (2:1) (salt) (8CI) Ergotartrat Gynergin Indolo[4,3-fg]quinoline, ergotaman-3',6',18-trione deriv. NSC 41869 KEFALGIN(R) (5'alpha)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-Ergotaman-3',6',18-trione, [R-(R*,R*)]-2,3-dihydroxybutanediate (2:1) (salt) Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha)-, [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:1) (salt) gotamine Medihaler-ergotamine (6aR,9R)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide 2,3-dihydroxysuccinate bis[(6aR,9R)-N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2- methyl-3,6-dioxo-octahydro-8H-oxazolo[3,2-a]pyrrolo[2,1- c]pyrazin-2-yl]-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3- fg]quinoline-9-carboxamide] tartrate ERGOTAMINE TARTRATE USP/EP/BP ergomar ergostat 379-79-3 C33H35N5O505C4H6O6 C70H76N10O16 C37H41N5O11 2C33H35N5O5C4H6O6 C66H70N10O10C4H6O6 C4H6O6C33H35N5O5 Heterocyclic Building Blocks Others Chiral Building Blocks Asymmetric Synthesis