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Bufotenine

Bufotenine structure

CAS No:
487-93-4
Formula:
C12H16N2O
Chemical Name:
Bufotenine
Synonyms:
1H-Indol-5-ol,3-[2-(dimethylamino)ethyl]-;Bufotenine;Indol-5-ol,3-[2-(dimethylamino)ethyl]-;3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol;Bufotenin;Cinobufotenine;3-(β-Dimethylaminoethyl)-5-hydroxyindole;N,N-Dimethyl-5-hydroxytryptamine;N,N-Dimethylserotonin;Mappine;5-Hydroxy-N,N-dimethyltryptamine;Dimethylserotonin;3-(2-Dimethylaminoethyl)indol-5-ol;Mappin;NSC 89593
Categories:
Analytical Chemistry > Standard

Description

Yellow Solid

Solid

Bufotenin is a tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. It has a role as a hallucinogen and a coral metabolite. It is a tryptamine alkaloid and a tertiary amine. It derives from a N,N-dimethyltryptamine.|Bufotenine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.|A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

Bufotenine Basic Attributes

Molecular Weight：

204.27

Exact Mass：

204.27

EC Number：

207-667-9

UNII：

0A31347TZK

DEA Code Number：

7433

NSC Number：

89593

DSSTox ID：

DTXSID0048894

HScode：

2933990090

Characteristics

PSA：

39.3

XLogP3：

1.97760

Appearance：

Solid

Density：

1.178g/cm3

Melting Point：

146.5 °C

Boiling Point：

bp0.1 320°

Flash Point：

2℃

Refractive Index：

1.646

Storage Conditions：

Refrigerator, Under Inert Atmosphere

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

1544

wgk germany：

hazard class code：

11-20/21/22-36

safety instructions：

16-36/37

Marks：

F,Xn

Precautionary statement(s)：

P210-P280-P305 + P351 + P338

Hazard Statements：

H225-H302 + H312 + H332-H319

Toxicity

Toxicity Summary：

Ingestion of Bufo toad venom and eggs by humans has resulted in several reported cases of poisoning, some of which resulted in death. The acute toxicity of bufotenin in rodents has been calculated to have an LD50 of between 200 and 300 mg/kg, which by comparison, is comparable to the LD50 for intravenous morphine (200-300 mg/kg) in mice. Respiratory arrest may occur, possibly leading to death.

Drug Information

Pharmacology：

Bufotenin is a tryptamine related to the neurotransmitter serotonin.

MeSH：

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)|Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)

Absorption：

Rapidly absorbed following intravenous administration.

Metabolism/Metabolites：

Upon oral administration, bufotenine is extensively metabolized by monoamine oxidase enzymes.|Bufotenine is a known human metabolite of n,n-dimethyl-5-methoxytryptamine.

MeSH Entry Terms：

5 Hydroxy N,N dimethyltryptamine

DEA Controlled Substances：

Bufotenine|Mappine, N,N-dimethylserotonin|7433|Schedule I - Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.|No

Bufotenine Use and Manufacturing

Uses

Controlled substance (hallucinogen).

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:204.27
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:204.126263138
Monoisotopic Mass:204.126263138
Topological Polar Surface Area:39.3
Heavy Atom Count:15
Complexity:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes