エセロリン

エセロリン
IUPAC命名法による物質名
	IUPAC名 (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol;
データベースID
CAS番号;	469-22-7
ATCコード	none
PubChem	CID: 119198
ChemSpider	106485
ChEBI	CHEBI:48845
別名	Eseroline
化学的データ
化学式	C13H18N2O
分子量	218.295 g/mol
	SMILES C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)O)C)C;
	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; Key:HKGWQUVGHPDEBZ-OLZOCXBDSA-N;
	テンプレートを表示

エセロリン(Eseroline)は、オピオイドアゴニストとして作用する薬剤である^[1]。アセチルコリンエステラーゼ阻害剤フィゾスチグミンの代謝物質であるが、フィゾスチグミンとは異なり、アセチルコリンエステラーゼ阻害作用は弱く、容易に逆行し^[2]^[3]、μ-オピオイド受容体に媒介されるかなり強い鎮痛剤効果を示す^[4]。この混合型の活性のため、エセロリンの薬理作用のプロファイルはかなり独特なものとなるが^[5]^[6]、低換気障害^[7]や神経毒性^[8]等の副作用のため、利用は限られている。

出典

^ Fürst, S; Friedmann, T; Bartolini, A; Bartolini, R; Aiello-Malmberg, P; Galli, A; Somogyi, GT; Knoll, J (1982). “Direct evidence that eseroline possesses morphine-like effects”. European Journal of Pharmacology 83 (3–4): 233–41. doi:10.1016/0014-2999(82)90256-4. PMID 6293841.
^ Jhamandas, K; Elliott, J; Sutak, M (1981). “Opiatelike actions of eseroline, an eserine derivative”. Canadian journal of physiology and pharmacology 59 (3): 307–10. PMID 7194726.
^ Galli, A; Renzi, G; Grazzini, E; Bartolini, R; Aiello-Malmberg, P; Bartolini, A (1982). “Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine”. Biochemical pharmacology 31 (7): 1233–8. doi:10.1016/0006-2952(82)90009-0. PMID 7092918.
^ Agresti, A; Buffoni, F; Kaufman, JJ; Petrongolo, C (1980). “Structure--activity relationships of eseroline and morphine: ab initio quantum-chemical study of the electrostatic potential and of the interaction energy with water”. Molecular Pharmacology 18 (3): 461–7. PMID 7464812.
^ Galli, A; Ranaudo, E; Giannini, L; Costagli, C (1996). “Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences”. The Journal of pharmacy and pharmacology 48 (11): 1164–8. doi:10.1111/j.2042-7158.1996.tb03914.x. PMID 8961166.
^ Liu, WF (1991). “Effect of eseroline on schedule-controlled behavior in the rat”. Pharmacology, Biochemistry, and Behavior 38 (4): 747–51. doi:10.1016/0091-3057(91)90236-U. PMID 1871191.
^ Berkenbosch, A; Rupreht, J; Degoede, J; Olievier, CN; Wolsink, JG (1993). “Effects of eseroline on the ventilatory response to CO2”. European Journal of Pharmacology 232 (1): 21–8. doi:10.1016/0014-2999(93)90723-U. PMID 8458393.
^ Somani, SM; Kutty, RK; Krishna, G (1990). “Eseroline, a metabolite of physostigmine, induces neuronal cell death”. Toxicology and applied pharmacology 106 (1): 28–37. doi:10.1016/0041-008X(90)90102-Z. PMID 2251681.

[1] Fürst, S; Friedmann, T; Bartolini, A; Bartolini, R; Aiello-Malmberg, P; Galli, A; Somogyi, GT; Knoll, J (1982). “Direct evidence that eseroline possesses morphine-like effects”. European Journal of Pharmacology 83 (3–4): 233–41. doi:10.1016/0014-2999(82)90256-4. PMID 6293841.

[2] Jhamandas, K; Elliott, J; Sutak, M (1981). “Opiatelike actions of eseroline, an eserine derivative”. Canadian journal of physiology and pharmacology 59 (3): 307–10. PMID 7194726.

[3] Galli, A; Renzi, G; Grazzini, E; Bartolini, R; Aiello-Malmberg, P; Bartolini, A (1982). “Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine”. Biochemical pharmacology 31 (7): 1233–8. doi:10.1016/0006-2952(82)90009-0. PMID 7092918.

[4] Agresti, A; Buffoni, F; Kaufman, JJ; Petrongolo, C (1980). “Structure--activity relationships of eseroline and morphine: ab initio quantum-chemical study of the electrostatic potential and of the interaction energy with water”. Molecular Pharmacology 18 (3): 461–7. PMID 7464812.

[5] Galli, A; Ranaudo, E; Giannini, L; Costagli, C (1996). “Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences”. The Journal of pharmacy and pharmacology 48 (11): 1164–8. doi:10.1111/j.2042-7158.1996.tb03914.x. PMID 8961166.

[6] Liu, WF (1991). “Effect of eseroline on schedule-controlled behavior in the rat”. Pharmacology, Biochemistry, and Behavior 38 (4): 747–51. doi:10.1016/0091-3057(91)90236-U. PMID 1871191.

[7] Berkenbosch, A; Rupreht, J; Degoede, J; Olievier, CN; Wolsink, JG (1993). “Effects of eseroline on the ventilatory response to CO2”. European Journal of Pharmacology 232 (1): 21–8. doi:10.1016/0014-2999(93)90723-U. PMID 8458393.

[8] Somani, SM; Kutty, RK; Krishna, G (1990). “Eseroline, a metabolite of physostigmine, induces neuronal cell death”. Toxicology and applied pharmacology 106 (1): 28–37. doi:10.1016/0041-008X(90)90102-Z. PMID 2251681.

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