Eseroline is an alkaloid found in the bark of the physostigma venenosum plant. It is a potent inhibitor of acetylcholinesterase, an enzyme that breaks down acetylcholine, a neurotransmitter. This inhibition leads to an accumulation of acetylcholine in the synaptic cleft, resulting in increased cholinergic activity. Eseroline has been shown to have various pharmacological effects, including muscle stimulation, increased salivation, and bronchoconstriction. It is a powerful tool for studying the role of acetylcholine in the nervous system and has potential therapeutic applications in the treatment of conditions such as Alzheimer's disease and myasthenia gravis. However, its use is limited due to its toxicity and narrow therapeutic window.'
eseroline: RN given refers to (3aS-cis)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
eseroline : 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 119198 |
| CHEMBL ID | 310934 |
| CHEBI ID | 48845 |
| SCHEMBL ID | 150460 |
| MeSH ID | M0078876 |
| Synonym |
|---|
| CHEMBL310934 , |
| (-)-eseroline |
| NCGC00142536-01 |
| pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3as,8ar)- |
| (3as-cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol |
| eseroline |
| (3as,8ar)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol |
| 469-22-7 |
| CHEBI:48845 , |
| (3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-ol |
| bdbm50292538 |
| unii-q22h41o18d |
| q22h41o18d , |
| NCGC00017362-02 |
| bdbm93695 |
| (3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrol[2,3-b]indol-7-ol;maleate |
| cid_45479742 |
| (3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-ol;(z)-but-2-enedioate |
| (3ar,8bs)-3,4,8b-trimethyl-2,3a-dihydro-1h-pyrrolo[2,3-b]indol-7-ol;(z)-2-butenedioate |
| SCHEMBL150460 |
| AKOS024282669 |
| pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3as,8ar)- |
| nih 10398 |
| mcv 4481 |
| eseroline, (-)- |
| (3as,8ar)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol |
| pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3as-cis)- |
| DTXSID30891448 |
| Q5397651 |
| eseroline-(-) |
Eseroline is a new agent, derived from physostigmine but lacking the pseudocholinesterase activity. Eseroline possesses opioid properties in vivo and in vitro in cats and rodents.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Eseroline is a new agent, derived from physostigmine but lacking in pseudocholinesterase activity, that possesses opioid properties in vivo and in vitro in cats and rodents. " | ( Inhibitory effect of eseroline, an opiate like drug, on the rat nociceptive thalamic neurons activated by peripheral noxious stimuli. Biella, G; Braga, PC; Dall'Oglio, G; Fraschini, F; Tiengo, M, 1984) | 2.03 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Eseroline not only has some structural features in common with morphine but also has a specific antinociceptive action like opioid drugs. " | ( Eseroline depresses the responses of dorsal horn neurons to C-fiber afferents in the spinal rat. Biella, G; Braga, PC; Fraschini, F; Tiengo, M, 1986) | 3.16 |
| Role | Description |
|---|---|
| opioid analgesic | A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. |
| human xenobiotic metabolite | Any human metabolite produced by metabolism of a xenobiotic compound in humans. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| phenols | Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring. |
| pyrroloindole | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 4.4563 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 6.3096 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 12.5893 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| TDP1 protein | Homo sapiens (human) | Potency | 10.4176 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 17.0390 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 12.4435 | 31.6228 | AID902; AID924 |
| Integrin beta-3 | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Integrin alpha-IIb | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 11.4157 | 31.6228 | AID924 |
| Inositol monophosphatase 1 | Rattus norvegicus (Norway rat) | Potency | 28.1838 | 1.0000 | 10.4756 | 28.1838 | AID1457 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID334454 | Displacement of [3H]U69593 from kappa opioid receptor in guinea pig cerebellum membrane | 1992 | Journal of natural products, Mar, Volume: 55, Issue:3 | Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors. |
| AID334452 | Displacement of [3H]pCl-DPDP from delta opioid receptor in rat central nervous system membrane | 1992 | Journal of natural products, Mar, Volume: 55, Issue:3 | Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors. |
| AID401020 | Analgesic activity in mouse by hot plate test | |||
| AID334453 | Displacement of [3H]DAMGO from mu opioid receptor in rat central nervous system membrane | 1992 | Journal of natural products, Mar, Volume: 55, Issue:3 | Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors. |
| AID107607 | Compound was tested in vivo for narcotic agonist activity (dose in sc, mg/kg) in mice using tail flick assay. | 1986 | Journal of medicinal chemistry, Nov, Volume: 29, Issue:11 | Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis. |
| AID107478 | Compound was tested in vivo for narcotic agonist activity (dose in sc, mg/kg) in mice using hot plate assay | 1986 | Journal of medicinal chemistry, Nov, Volume: 29, Issue:11 | Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis. |
| AID44276 | Anticholinesterase activity against plasma Butyrylcholinesterase (BChE) in humans.(no detectable activity at 3*10e-5 M) | 1998 | Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13 | Syntheses and anticholinesterase activities of (3aS)-N1, N8-bisnorphenserine, (3aS)-N1,N8-bisnorphysostigmine, their antipodal isomers, and other potential metabolites of phenserine. |
| AID107604 | Compound was tested in vivo for narcotic agonist activity (dose in sc, mg/kg) in mice using phenylquinone assay. | 1986 | Journal of medicinal chemistry, Nov, Volume: 29, Issue:11 | Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis. |
| AID107610 | Compound was tested in vivo for narcotic antagonist activity (dose in sc, mg/kg) in mice using tail flick antagonism assay; I = Inactive at 1,10, 30 mg/kg | 1986 | Journal of medicinal chemistry, Nov, Volume: 29, Issue:11 | Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis. |
| AID31016 | Anticholinesterase activity against erythrocyte acetylcholinesterase (AChE) in humans.(no detectable activity at 3*10e-5 M) | 1998 | Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13 | Syntheses and anticholinesterase activities of (3aS)-N1, N8-bisnorphenserine, (3aS)-N1,N8-bisnorphysostigmine, their antipodal isomers, and other potential metabolites of phenserine. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 15 (55.56) | 18.7374 |
| 1990's | 7 (25.93) | 18.2507 |
| 2000's | 4 (14.81) | 29.6817 |
| 2010's | 1 (3.70) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (24.00) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 29 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||