기본 정보
- CAS
469-22-7- 표준 SMILES
CN1CC[C@@]2(C)c3cc(O)ccc3N(C)[C@@H]12- InChIKey
HKGWQUVGHPDEBZ-OLZOCXBDSA-N- 분자식
- C13H18N2O
- 평균 분자량
- 218.29 g/mol
- 단동위원소 질량
- 218.1419132
개요
Eseroline is a pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP. It has a role as an opioid analgesic and a human xenobiotic metabolite. It is a member of phenols and a pyrroloindole.
이름 및 식별자
- 우선 이름
- Eseroline
- IUPAC
- (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol
- 현지명
- 에세롤린
- 영어명
- Eseroline
- 분자식
- C13H18N2O
- 분자량
- 218.29
이름 및 동의어
Eseroline469-22-7(-)-Eseroline(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-olDTXSID30891448Q22H41O18DCHEBI:48845MCV 4481(3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-olNIH 10398Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-ol
이름 더 보기
에세롤린(3aS)-1,2,3,3a,8,8a-Hexahydro-1,3aα,8α-trimethylpyrrolo[2,3-b]indol-5-ol(-)-Eseroline DISCONTINUED. Offer only E889163
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-RefChem:137866DTXCID801030561(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-olCHEMBL310934eseroline-(-)ESEROLINE, (-)-SCHEMBL150460
데이터베이스 식별자
- CAS
469-22-7
물성
구조 계산 물성
- XLogP
- 0.8
- 극성 표면적
- 26.7 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 16
- 형식 전하
- 0
- 복잡도
- 296
실험 및 물리화학적 성질
Collision Cross Section
149.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
141.83 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 128 °C · 128 °C
- 끓는 점
- 366.3 · 366.3±42.0 °C(Predicted)
- 밀도
- 1.16 · 1.160±0.06 g/cm3(Predicted)
- 산도 계수 (pKa)
- 10.17 · 10.17±0.40(Predicted)
- InChI
- InChI=1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3/t12-,13+/m1/s1
- InChIKey
- HKGWQUVGHPDEBZ-OLZOCXBDSA-N
- SMILES
- N1(C)C2=C(C=C(O)C=C2)[C@]2(C)CCN(C)[C@]12[H]
화학적 성질
Physostigmine crystals or solutions, when heated, exposed to light and air, or in the presence of traces of metal, readily turn red, are more unstable to bases, and are readily hydrolyzed to eserobine, which are capable of being oxidized to red physostigmine salicylate, depriving the product of its therapeutic efficacy.
화학 및 산업
약리 정보
MeSH Pharmacological ClassificationCompounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
응용 분야
개요Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor.
출처Eseroline, although derived from physostigmine by hydrolysis of N-methylcarbamoil group, is also structurally related to morphine.
용도(-)-Eseroline is a metabolite of physostigmine, displaying both anti-acetylcholinesterase and opiate agonist activities.
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