Tiomergine

Tiomergine (INNTooltip International Nonproprietary Name; developmental code name CF 25-397) is a dopamine receptor agonist of the ergoline family which was never marketed.^[1][2][3][4] It is an analogue of the antiparkinsonian agent pergolide.^[1][2]

Other namesCF 25-397; CF25-397; CF-25397; CF25397; 9,10-Didehydro-6-methyl-8β-((2-pyridylthio)methyl)ergoline

Drug classDopamine receptor agonist; Serotonin receptor agonist

ATC code

• None

CAS Number

• 57935-49-6

Quick facts Clinical data, Other names ...

Tiomergine

Clinical data
Other names	CF 25-397; CF25-397; CF-25397; CF25397; 9,10-Didehydro-6-methyl-8β-((2-pyridylthio)methyl)ergoline
Drug class	Dopamine receptor agonist; Serotonin receptor agonist
ATC code	None
Identifiers
IUPAC name (6aR,9R)-7-methyl-9-(pyridin-2-ylsulfanylmethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
CAS Number	57935-49-6
PubChem CID	9884658
DrugBank	DB20293
ChemSpider	8060332
UNII	85J22V47HN
ChEMBL	ChEMBL2104731
CompTox Dashboard (EPA)	DTXSID901024153
Chemical and physical data
Formula	C21H21N3S
Molar mass	347.48 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)CSC5=CC=CC=N5
InChI InChI=1S/C21H21N3S/c1-24-12-14(13-25-20-7-2-3-8-22-20)9-17-16-5-4-6-18-21(16)15(11-23-18)10-19(17)24/h2-9,11,14,19,23H,10,12-13H2,1H3/t14-,19-/m1/s1 Key:VCRAKEDGLIINLR-AUUYWEPGSA-N

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In addition to its dopamine receptor agonism, tiomergine also acts as a potent serotonin receptor agonist, including binding to serotonin 5-HT₁ and 5-HT₂ receptors, and might actually act primarily via its serotonin receptor agonism.^[5][6][7][8] The drug produces antiparkinsonian-like effects in rodents.^[9] In contrast to other dopamine receptor agonists however, it produces little to no stereotypy.^[9] In addition, tiomergine produces little change in locomotor activity on its own but reverses reserpine-induced catalepsy.^[9] Unlike many other dopamine receptor agonists like pergolide, tiomergine has been identified as a selective or preferential dopamine autoreceptor agonist, with little activity at postsynaptic receptors.^[10][11][12]

In contrast to animal studies, tiomergine caused severe deterioration in parkinsonism symptoms in humans in a clinical trial.^[13][14] It was also ineffective in treating psychosis in people with schizophrenia.^[15] Besides these uses, tiomergine has been investigated for the treatment of dyskinesia and dystonia.^[16][17] However, it was ineffective for tardive dyskinesia as well.^[17]

Tiomergine was first described in the scientific literature by 1976.^[9] It was developed by Sandoz.^[3]