Molecular Identity
Dihydroergotamine
(6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID: 10531
Dihydroergotamine is ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension. It has a role as a non-narcotic analgesic, a serotonergic agonist, a vasoconstrictor agent, a dopamine agonist and a sympatholytic agent. It is an ergot alkaloid and a semisynthetic derivative.
2D Structure
Properties
C33H37N5O5
Molecular Formula
583.70
Molecular Weight
g/mol
583.2795
Exact Mass
Da
2.4
XLogP
Drug-like (Lipinski: < 5)
118
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
6
H-Bond Acceptors
1160
Complexity
SMILES
Canonical SMILES
SMILES: CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(CC7=CNC8=CC=CC6=C78)N(C5)CIsomeric SMILES
SMILES: C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@@H]5C[C@H]6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)CSynonyms(20)
dihydroergotamine511-12-69,10-DihydroergotamineDihidroergotaminaDihydroergotaminumNeomigranDiidroergotaminaAgitMAP0004DTXSID6045614MAP-0004436O5HM03CCHEBI:4562DTXCID40256145'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Dihydroergotamine
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