기본 정보
- CAS
520-53-6- 표준 SMILES
CN(C)CCc1c[nH]c2cccc(O)c12- InChIKey
SPCIYGNTAMCTRO-UHFFFAOYSA-N- 분자식
- C12H16N2O
- 평균 분자량
- 204.27 g/mol
- 단동위원소 질량
- 204.12626314
개요
Psilocin is a tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonancatl or "magic mushrooms"). It has a role as a hallucinogen, a serotonergic agonist, a drug metabolite, a fungal metabolite and a human xenobiotic metabolite. It is a member of phenols, a tryptamine alkaloid, a tertiary amino compound and a member of hydroxyindoles. It is functionally related to a N,N-dimethyltryptamine. It is a conjugate base of a psilocinium.
이름 및 식별자
- 우선 이름
- Psilocin
- IUPAC
- 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
- 영어명
- PSILOCIN
- 분자식
- C12H16N2O
- 분자량
- 204.27
이름 및 동의어
PSILOCINPsilocine4-Hydroxy-N,N-dimethyltryptaminePsilotsinPsilocyn520-53-63-[2-(Dimethylamino)ethyl]-1H-indol-4-ol3-(2-(Dimethylamino)ethyl)indol-4-ol4-HO-DMTN,N-Dimethyl-4-HydroxytryptamineDTXSID5048899CMS88KUW0G
이름 더 보기
CX 59cx-59psylocinGMP Psilocin4-hydroxy DMTPsilocin (CRM)
3-(2-(Dimethylamino)ethyl)-1H-indol-4-olCHEBI:8613DTXCID5028825(3-(2-dimethylamino)ethyl)indol-4-olRefChem:870285208-296-5CHEMBL655471H-Indol-4-ol, 3-[2-(dimethylamino)ethyl]-
데이터베이스 식별자
- CAS
520-53-6- PubChem CID
- 4980
- DTXSID
DTXSID5048899- ChEMBL
CHEMBL65547- ChEBI
CHEBI:8613- UNII
- CMS88KUW0G
- EC Number
- 208-296-5
- Nikkaji
- J12.982H
물성
구조 계산 물성
- XLogP
- 2.1
- 극성 표면적
- 39.3 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 15
- 형식 전하
- 0
- 복잡도
- 208
실험 및 물리화학적 성질
Drugs
DEA NFLIS-Drug Category -> Psychedelics
DEA Schedule I Controlled Substance -> Hallucinogenic substances
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Human DrugsPharmaceuticals
Melting Point174.5 °C
Physical DescriptionSolid
Collision Cross Section144.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
물리화학적 성질
- 녹는점
- 173 · 173-176°
- 끓는 점
- 342.77 °C · 342.77°C (rough estimate)
- 밀도
- 1.0565 · 1.0565 (rough estimate)
- 굴절률
- 1.6 · 1.6000 (estimate)
- 인화점
- 11 °C · 11 °C
- 저장 조건
- 20 °C · −20°C
- 용해도
- 100 mM · Soluble to 100 mM in DMSO
- 산도 계수 (pKa)
- 10.01 · 10.01±0.40(Predicted)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
유해성 정보
Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
Health EffectsPsilocin is neurotoxic and can cause hallucinations. (L1673)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryPsilocin acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). It is an 5-HT1A and 5-HT2A/2C agonist. (L1673)
Signs and SymptomsPsilocin may cause tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals, synesthesia, increased body temperature, headache, sweating and chills, and nausea. (L1673)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
안전 데이터
- wgk
- 3
- rtecs
- NM2625000
- ridadr
- UN 1230 3/PG 2
- 독성
- LD50 intraperitoneal in mouse: 196mg/kg
- risk_code
- 22-39/23/24/25-23/24/25-11
- hazard_code
- Xn,T,F
- safety_code
- 36/37/39-45-36/37-16-7
- 포장분류
- III
- 위험 등급
- 6.1(b)
화학 및 산업
약리 정보
Metabolism/MetabolitesPsilocin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification
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.
용도 및 제조
Uses
Psilocin is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms. (L1673)
Use ClassificationPharmaceuticals
응용 분야
용도The 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).
추가 설명
정의An indole derivative. An alkaloid from certain mush- rooms; a hallucinogenic drug.
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