CAS 487-93-4|mappin|Bufotenine|Bufotenine|3-[2-(dimethylamino)ethyl]-1H-indol-5-ol|N,N-dimethyl-5-hydroxytryptamine|cebilcin|5-hydroxy-dimethyltryptamine|Bufotenin|Cinobufotenine|NSC 89593|5-Hydroxy...

General Information

Structure

Molecular Formula

C₁₂H₁₆N₂O

Molecular Mass

204.26824

Exact Mass

204.12626314

Charge

InChI

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

InChIKey

VTTONGPRPXSUTJ-UHFFFAOYSA-N

Canonic Smiles

CN(CCc1c[nH]c2c1cc(O)cc2)C

Isomeric Smiles

Oc1cc2c(CCN(C)C)c[nH]c2cc1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.29

LogD (pH = 5.5)

-1.42

Log P

1.25

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.00

Polar Surface Area

39.26

Polarizability

23.40

Molar Refractivity

62.42

LOG S

-1.60

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

IUPAC Traditional name

mappin bufotenine

Synonyms

BufotenineBufotenineN,N-dimethyl-5-hydroxytryptaminecebilcinBufotenin5-hydroxy-dimethyltryptamineMappin3-[2-(Dimethylamino)ethyl]-1H-indol-5-olCinobufotenineBufoteninN,N-Dimethylserotonin3-(β-Dimethylaminoethyl)-5-hydroxyindoleMappineNSC 895935-Hydroxy-N,N-dimethyltryptamineDimethylserotoninN,N-DimethylserotoninN,N-dimethylserotoninDM5-HTBufoteninebufoteninBufotenin3-[2-(dimethylamino)ethyl]indol-5-ol5-hydroxy-N,N-dimethyltryptamine3-[beta-(dimethylamino)ethyl]-5-hydroxyindole3-[2-(dimethylamino)ethyl]-5-indolol

IUPAC name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Names and Identifiers

Registration numbers

PubChem SID

4650717416096471146530531

PubChem CID

CAS Number

KEGG ID

IUPHAR ligand ID

CHEBI ID

DrugBank ID

Wikipedia Title

CHEMBL

Chemspider ID

MetaboLights Database

MTBLS1693MTBLS406MTBLS804MTBLS2267

Beilstein Number

160628

PubMed Citation Links

874715720206139117183208532147160950481930323065812520150873409102788951122162438720942780

BRENDA Database

3.5.1.132.1.1.42.1.1.8

CompTox Database

DTXSID0048894

NMRShiftDB Database

20026032

SureChEMBL Database

SCHEMBL518028

Patent number

WO2005039546US2008293695EP1829527

Reaxys Registry

160628

KNApSAcK Database

C00001402

BRENDA Ligand Database

ACToR Database

BKMS React Database

BindingDB Database

Registration numbers

Properties

Physical Property

Pharmacology Properties

Schedule I (US)

Parenteral

Product Information

Download link

Safety Information

Refrigerator, Under Inert Atmosphere

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01445

Drug Groups

illicit; experimental

Description

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.

Pharmacology

Bufotenin is a tryptamine related to the neurotransmitter serotonin.

Toxicity

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. Death occurs by respiratory arrest.

Affected Organisms

Humans and other mammals

Biotransformation

Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.

Absorption

Rapidly absorbed following intravenous administration.

References

• Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. [Pubmed]

• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [Pubmed]

• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [Pubmed]

• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [Pubmed]

• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [Pubmed]

External Links

• [Wikipedia]

Wikipedia

Bufotenin

TRC

B689525

Controlled substance (hallucinogen).

ChEBI

CHEBI:3210

A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5.

Molecule Details

References

PubChem Literature

From Data Sources

• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. Pubmed

• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. Pubmed

• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. Pubmed

• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. Pubmed

• Bhattacharya, S., et al.: Indian. J. Physiol. Pharmacol., 15, 133 (1955)

• Falkenberg, G., et al.: Acta Crystallogr., 28B, 3219 (1955)

• Stoll, et al.: Helv. Chim. Acta, 38, 1452 (1955)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

IUPAC Traditional name

mappin bufotenine

Synonyms

IUPAC name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Registration numbers

PubChem SID

4650717416096471146530531

PubChem CID

CAS Number

KEGG ID

IUPHAR ligand ID

CHEBI ID

DrugBank ID

Wikipedia Title

CHEMBL

Chemspider ID

MetaboLights Database

MTBLS1693MTBLS406MTBLS804MTBLS2267

Beilstein Number

160628

PubMed Citation Links

874715720206139117183208532147160950481930323065812520150873409102788951122162438720942780

BRENDA Database

3.5.1.132.1.1.42.1.1.8

CompTox Database

DTXSID0048894

NMRShiftDB Database

20026032

SureChEMBL Database

SCHEMBL518028

Patent number

WO2005039546US2008293695EP1829527

Reaxys Registry

160628

KNApSAcK Database

C00001402

BRENDA Ligand Database

ACToR Database

BKMS React Database

BindingDB Database

Molecule Details

DB01445

Drug Groups

illicit; experimental

Description

Pharmacology

Bufotenin is a tryptamine related to the neurotransmitter serotonin.

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Orally administered bufotenine undergoes extensive first-pass metabolism by the enzyme monoamine oxidase.

Absorption

Rapidly absorbed following intravenous administration.

References

• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. [Pubmed]

• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. [Pubmed]

• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [Pubmed]

• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [Pubmed]

External Links

• [Wikipedia]

Wikipedia

Bufotenin

TRC

B689525

Controlled substance (hallucinogen).

ChEBI

CHEBI:3210

A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5.

References

PubChem Literature

From Data Sources

• Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. Pubmed

• Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism] Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. Pubmed

• Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. Pubmed

• Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. Pubmed

• Bhattacharya, S., et al.: Indian. J. Physiol. Pharmacol., 15, 133 (1955)

• Falkenberg, G., et al.: Acta Crystallogr., 28B, 3219 (1955)

• Stoll, et al.: Helv. Chim. Acta, 38, 1452 (1955)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Pharmacology Properties

Schedule I (US)

Parenteral

Product Information

Download link

Safety Information

Refrigerator, Under Inert Atmosphere

Download link

Molecule

ID:1251