ERGOTAMINE TARTRATE Chemical 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)

EPA Substance Registry System

Ergotamine tartrate (379-79-3)

Safety Information

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

F 

3-8-10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29396200

ERGOTAMINE TARTRATE Usage And Synthesis

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

Ergotamine tartrate is a crystalline solid.

Chemical Properties

White 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

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin,remove contaminated clothing and wash immediately withsoap and water. Speed in removing material from skin is ofextreme importance. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure, beginrescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heartaction has stopped. Transfer promptly to a medical facility.When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Donot make an unconscious person vomit. Keep victim quietand maintain normal body temperature. Effects may bedelayed; keep victim under observation.

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area.

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

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