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520-53-6 molecular structure
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3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

ChemBase ID: 130311
Molecular Formular: C12H16N2O
Molecular Mass: 204.26824
Monoisotopic Mass: 204.12626314
SMILES and InChIs

SMILES:
Oc1cccc2c1c(c[nH]2)CCN(C)C
Canonical SMILES:
CN(CCc1c[nH]c2c1c(O)ccc2)C
InChI:
InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
InChIKey:
SPCIYGNTAMCTRO-UHFFFAOYSA-N

Cite this record

CBID:130311 http://www.chembase.cn/molecule-130311.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
IUPAC Traditional name
psilocin
Synonyms
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
Psilocyn
Psilocin solution
4-hydroxy-''N'',''N''-dimethyltryptamine
Psilocin
4-Hydroxy-N,N-dimethyltryptamine
Psilocin
4-羟基-N,N-二甲基色胺 溶液
4-羟基-N,N-二甲基色胺
CAS Number
520-53-6
EC Number
200-659-6
208-296-5
MDL Number
MFCD00079228
PubChem SID
162224590
24898489
24898305
PubChem CID
4980
CHEBI ID
8613
CHEMBL
65547
Chemspider ID
4807
KEGG ID
C08312
Wikipedia Title
Psilocin

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.971079  H Acceptors
H Donor LogD (pH = 5.5) -1.3831663 
LogD (pH = 7.4) -0.095287494  Log P 1.1496978 
Molar Refractivity 62.4231 cm3 Polarizability 25.000689 Å3
Polar Surface Area 39.26 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
173-176 °C (343.4-348.8°F) expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
RTECS
NM2625000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1230 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
1 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
22 expand Show data source
Safety Statements
36/37/39 expand Show data source
7-16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H301-H311-H331-H370 expand Show data source
H302 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1230 3/PG 2 expand Show data source
Drug Control
Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland expand Show data source
USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
Oral, IV expand Show data source
Excretion
Kidneys/Urine expand Show data source
Half Life
2–3 hours expand Show data source
Metabolism
Liver expand Show data source
Legal Status
Class A(NZ)
Class A(UK)
expand Show data source
S9 (Australia) expand Show data source
Schedule I (US) expand Show data source
Schedule III (Canada) expand Show data source
Gene Information
human ... HTR1A(3350)rat ... Htr2a(29595), Htr2c(25187) expand Show data source
Concentration
100 μg/mL in methanol expand Show data source
Grade
drug standard expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - P2279 external link
Biochem/physiol Actions
Hallucinogen originally isolated from the mushroom, Psilocybe mexicana, non-selective serotonin receptor agonist.
Toronto Research Chemicals - P839630 external link
The minor hallucinogenic component of the Teonanacatl mushroom. Psilocin is the 4-hydroxy analog of Psilocybin, formed by metabolic dephosphorylation of Psilocybin and is an active neurochemical. Psychomimetic. Controlled substance (hallucinogen).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hofmann, et al.: Experientia, 14, 397 (1958)
  • • Callahan, P., et al.: J. Pharmacol. Exp. Ther., 246, 866 (1958)
  • • Appel, J., et al.: Eur. J. Pharmacol., 159, 41 (1958)
  • • Blair, J., et al.: J. Med. Chem., 43, 4701 (1958)
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PATENTS

PATENTS

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INTERNET

INTERNET

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