Tochergamine
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| Other names | 621 I.S.; N,N-Diethyl-N′-(1,2,3,4-tetrahydronaphthyl)-glycinamide; Tochergamina |
| Routes of administration | Parenteral (e.g., intravenous injection, intramuscular injection) |
| Drug class | Oxytocic |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C16H24N2O |
| Molar mass | 260.381 g·mol−1 |
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Tochergamine, also known as 621 I.S. or as N,N-diethyl-N′-(1,2,3,4-tetrahydronaphthyl)glycinamide, is an oxytocic drug related to ergometrine which does not appear to have been marketed.[1][2]
It was reported to be effective as an oxytocic agent in animal studies, with oxytocic activity equivalent to that of ergometrine.[3] In addition, the drug was reported to be effective in clinical studies at doses of 2 to 6 mg parenterally.[2][4][5] However, subsequent research found that it was inactive on the intact human uterus at doses of up to 20 mg, and further investigation of tochergamine was abandoned.[3][2]
Tochergamine has a simplified lysergamide-like chemical structure, with a 1-aminotetralin ring system, and is structurally related to lysergamides like ergometrine and LSD.[1][6] However, it is not technically a partial ergoline or lysergamide, only partial ergoline-like, as its structural features differ in certain regards from those of ergolines and lysergamides.[1][6] The oxytocic effects of lysergamides like ergometrine are thought to most likely be mediated by agonism of serotonin 5-HT2 receptors in uterine smooth muscle tissue.[7][8]
Tochergamine was first described in the scientific literature in 1951.[4] It was developed by Daniel Bovet and colleagues at the Istituto Superiore di Sanità in Rome, Italy.[2][4] The drug was known as tochergamina in Italy.[4] It was clinically studied as an oxytocic agent in the 1950s.[2][4][9][5][10]
Analogues of tochergamine, for instance the 2-aminotetralin positional isomer, have also been described, and have likewise shown oxytocic and lysergic acid-like activity.[11]
See also
[edit | edit source]References
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- ^ a b Bravo, R. R. (1952). Clinical observations on the use of a new synthetic oxytocic drug: N2, N2-diethyl-N1-(1, 2, 3, 4-tetrahydronaphthyl) glycinamide (621 IS). Rend. Ist. Super. Sanita, 15, 1008. https://scholar.google.com/scholar?cluster=5046197701730900775 https://eurekamag.com/research/025/706/025706975.php "The activity of 621 I.S. was observed in 101 cases of normal or surgical birth. The drug is active in doses of 2-6 mg. given either intraven., intramusc, or intra-parietally. Given immediately after parturition it promotes expulsion of the placenta, causing a contraction of the uterus and controlling hemorrhage to within normal limits. Intraven. injn. of 2 mg. produces a prolonged rather than an immediate action and may be used prophylactically. The same dose intraven. is sufficient to obtain good hemostasis, at least in patients without unfavorable conditions (narcosis from ether, for example) in whom doses of 4 and 6 mg. are required. Intraparietal use is particularly important in cesarean section. In 11 cases the uterine reaction occurred in a more than satisfactory manner. In 3 cases in which 6 mg. was given intraven. there was pain in the hypogastric region following intense uterine contraction. The drug has a high margin of tolerance, does not change arterial pressure, and does not produce local effects."
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