Tertiary alcohols

Dienogest, sold under the brand name Visanne (manufactured by Bayer AG) among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis. It is also used in menopausal hormone therapy and to treat heavy periods. Dienogest is available both alone and in combination with estrogens. It is taken by mouth.

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxide and is thought to possess fixative properties for other odorants.

chemical compound

Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.

Hematein (US spelling) or haematein is an oxidized derivative of haematoxylin, used in staining. Haematein should not be confused with haematin, which is a brown to black iron-containing pigment formed by decomposition of haemoglobin. In the Colour Index (but nowhere else), haematein is called haematine.

Nerolidol, also known as peruviol and penetrol, is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers. There are four isomers of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers. Nerolidyl derivatives include nerolidyl di

thumb|Unlike the typical 6-6-6-5 steroid ring backbone (1), veratridine displays a 6-6-5-6 arrangement (2).Veratridine is a steroidal alkaloid found in plants related to lilies, specifically the genera Veratrum and Schoenocaulon. Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the inactivation of voltage-gated sodium ion channels in heart, nerve, and skeletal muscle cell membranes. Veratridine increases nerve excitability and intracellular Ca2+ concentrations.

Megestrol (, ) is a progestin of the 17α-hydroxyprogesterone group which was, until recently, never marketed or used clinically. It is now used for treatments of disease-related weight loss, endometrial cancer, and breast cancer. Its acylated derivative megestrol acetate is also a progestogen, which, in contrast to megestrol itself, has been extensively used as a pharmaceutical drug.

Forskolin (coleonol) is a labdane diterpene produced by the plant Coleus barbatus (blue spur flower). Other names include pashanabhedi, Indian coleus, makandi, HL-362, mao hou qiao rui hua. As with other members of the large diterpene class of plant metabolites, forskolin is derived from geranylgeranyl pyrophosphate (GGPP). Forskolin contains some unique functional elements, including the presence of a tetrahydropyran-derived heterocyclic ring.

3-Methyl-3-pentanol (IUPAC name: 3-methylpentan-3-ol) is an organic chemical compound and a tertiary hexanol. It is used in the synthesis of the tranquilizer emylcamate, and has similar sedative and anticonvulsant actions itself.

Norgestrel, sold under the brand name Opill among others, is a progestin which is used in birth control pills. It is often combined with the estrogen ethinylestradiol, marketed as Ovral. It is also used in menopausal hormone therapy. It is taken by mouth.

Cyproterone, also known by its developmental code name SH-80881, is a steroidal antiandrogen which was studied in the 1960s and 1970s but was never introduced for medical use. It is a precursor of cyproterone acetate (CPA), an antiandrogen, progestin, and antigonadotropin which was introduced instead of cyproterone and is widely used as a medication. Cyproterone and CPA were among the first antiandrogens to be developed.

Midecamycin is a macrolide antibiotic that is synthesized from Streptomyces mycarofaciens.

Acetorphine is a potent opioid analgesic, up to 8700 times stronger than morphine by weight. It is a derivative of the more well-known opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos.

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia, Parkinson's disease, and idiopathic or secondary dystonia.

2-Methyl-2-pentanol (IUPAC name: 2-methylpentan-2-ol) is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.

Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris (Senecio jacobaea). It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.

chemical compound

Brazilin is a naturally occurring, homoisoflavonoid, red dye obtained from the wood of Paubrasilia echinata, Biancaea sappan, Caesalpinia violacea, and Haematoxylum brasiletto (also known as Natural Red 24 and CI 75280). Brazilin has been used since at least the Middle Ages to dye fabric, and has been used to make paints and inks as well. The specific color produced by the pigment depends on its manner of preparation: in an acidic solution brazilin will appear yellow, but in an alkaline preparation it will appear red. Brazilin is closely related to the blue-black dye precursor hematoxylin, hav

7-Hydroxymitragynine (7-OH-MIT, often simply referred to as 7-OH) is a terpenoid indole alkaloid present in the plant Mitragyna speciosa (the leaves of which are commonly known as kratom). It was first described in 1994. In humans, it is produced as an active metabolite of mitragynine via hepatic oxidation.

Trifluperidol is a typical antipsychotic of the butyrophenone chemical class. It has general properties similar to those of haloperidol, but is considerably more potent by weight, and causes relatively more severe side effects, especially tardive dyskinesia and other extrapyramidal effects. It is used in the treatment of psychoses including mania and schizophrenia. It was discovered at Janssen Pharmaceutica in 1959.

Pipradrol, also known by its brand name Meratran, is a mild central nervous system stimulant that acts as a norepinephrine-dopamine reuptake inhibitor. Developed in the United States in the 1940s and patented in 1953, pipradrol was initially marketed as an antidepressant in the mid-1950s. It was subsequently used as an adjunct treatment for various conditions, including obesity, senile dementia, narcolepsy, and schizophrenia.

Methylpentynol (also known as methylparafynol, trade names Dormison, Atemorin, Oblivon) is a tertiary pentynol with hypnotic/sedative and anticonvulsant effects and an exceptionally low therapeutic index. It was discovered by Bayer in 1913 and was used shortly thereafter for the treatment of insomnia, but its use was quickly phased out in response to newer drugs with far more favorable safety profiles.

Penfluridol (Semap, Micefal, Longoperidol) is a highly potent, first generation diphenylbutylpiperidine antipsychotic. It was discovered at Janssen Pharmaceutica in 1968. Related to other diphenylbutylpiperidine antipsychotics, pimozide and fluspirilene, penfluridol has an extremely long elimination half-life and its effects last for many days after single oral dose. Its antipsychotic potency, in terms of dose needed to produce comparable effects, is similar to both haloperidol and pimozide. It is only slightly sedative, but often causes extrapyramidal side-effects, such as akathisia, dyskines

Delphinine is a toxic diterpenoid alkaloid found in plants from the Delphinium (larkspur) and Atragene (a clematis) genera, both in the family Ranunculaceae. Delphinine is the principal alkaloid found in Delphinium staphisagria seeds – at one time, under the name stavesacre, a very well known herbal treatment for body lice. It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing low blood pressure, slowed heart rate and abnormal heart rhythms. These effects make it highly poisonous ( 1.5–3.0 mg/kg i

Tibolone, sold under the brand name Livial among others, is a medication which is used in menopausal hormone therapy and in the treatment of postmenopausal osteoporosis and endometriosis. The medication is available alone and is not formulated or used in combination with other medications. It is taken by mouth.

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.

Isavuconazonium, sold under the brand name Cresemba, is a systemic antifungal medication of the triazole class which is used to treat invasive aspergillosis and mucormycosis. It is used as the sulfate. It is taken by mouth or given via injection into a vein.

Methylnaltrexone (MNTX, brand name Relistor), used in form of methylnaltrexone bromide (INN, USAN, BAN), is a medication that acts as a peripherally acting μ-opioid receptor antagonist that acts to reverse some of the side effects of opioid drugs such as constipation without significantly affecting pain relief or precipitating withdrawals. Because MNTX is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as pain r

thumb|The Phyla dulcis plant, which naturally produces hernandulcin. Hernandulcin is an intensely sweet chemical compound gained from the chiefly Mexican and South American plant Lippia dulcis.

Hydroxy-α-sanshool (), also known as simply sanshool is a molecule found in plants from the genus Zanthoxylum. It is believed to be responsible for the numbing and tingling sensation caused by eating food cooked with Sichuan peppercorns and Uzazi.

Humulone (α-lupulic acid), a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops (Humulus lupulus). Humulone is a prevalent member of the class of compounds known as alpha acids, which collectively give hopped beer its characteristic bitter flavor.

Bromperidol, sold under the brand names Bromidol and Impromen among others, is a typical antipsychotic of the butyrophenone group which is used in the treatment of schizophrenia. It was discovered at Janssen Pharmaceutica in 1966. An ester prodrug, bromperidol decanoate, is a long-acting form of bromperidol used as a depot injectable.

Clobutinol is a cough suppressant formerly distributed by Boehringer Ingelheim and its licensees under the names Lomisat and Silomat, by Bioter as Biotussin, and by Violani-Farmavigor as Pertoxil. It has been withdrawn from the market worldwide.

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. A phytoecdysteroid produced by and extracted from various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides, it is thought to be a plant defense against herbivory that disrupts the reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals (including humans) lack this recep

Chlorodehydromethyltestosterone (CDMT; brand name Oral Turinabol), also known as 4-chloro-17β-hydroxy17α-methylandrosta-1,4-dien-3-one, is an anabolic–androgenic steroid (AAS). It is the 4-chloro-substituted derivative of metandienone (dehydromethyltestosterone).

Thapsigargin is a non-competitive inhibitor of the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA). Structurally, thapsigargin is classified as a guaianolide, and is extracted from a plant, Thapsia garganica. It is a tumor promoter in mammalian cells.

Evoxine (haploperine) is a furoquinoline alkaloid with hypnotic and sedative effects. It is found naturally in a variety of Australian and African plants including Evodia xanthoxyloides and Teclea gerrardii.

Cubebol is a natural sesquiterpene alcohol first identified in cubeb oil. It is also found in basil. It was patented as a cooling agent in 2001 by Firmenich, an international flavor company. The taste of cubebol is cooling and refreshing. The patent describes application of cubebol as a refreshing agent in various products, ranging from chewing gum to sorbets, drinks, toothpaste, and gelatin-based confectioneries.

The calicheamicins are a class of enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora, with calicheamicin γ1 being the most notable. It was isolated originally in the mid-1980s from the chalky soil, or "caliche pits", located in Kerrville, Texas. The sample was collected by a scientist working for Lederle Labs. It is extremely toxic to all cells and, in 2000, a CD33 antigen-targeted immunoconjugate N-acetyl dimethyl hydrazide calicheamicin was developed and marketed as targeted therapy against the non-solid tumor cancer acute myeloid leukemia (AML). A second ca

chemical compound

Allylestrenol, sold under the brand names Gestanin and Turinal among others, is a progestin medication which is used to treat recurrent and threatened miscarriage and to prevent premature labor in pregnant women. However, except in the case of proven progesterone deficiency, its use for such purposes is no longer recommended. A Cochrane review in 2025 found that it had little to no effect in subsequent pregnancy outcomes for women with unexplained, recurrent miscarriage. It is also used in Japan to treat benign prostatic hyperplasia (BPH) in men. The medication is used alone and is not formula

chemical compound

Lynestrenol, sold under the brand names Exluton and Ministat among others, is a progestin medication which is used in birth control pills and in the treatment of gynecological disorders. The medication is available both alone and in combination with an estrogen. It is taken by mouth.

Hydroxycitronellal (7-hydroxy-3,7-dimethyloctanal) is an odorant used in perfumery. Its molecular formula is C10H20O2.

Hydroxymethylpentylcyclohexenecarboxaldehyde (HMPCC) is a synthetic fragrance known by the trade names Lyral, Kovanol, Mugonal, Landolal. It is found in some soaps, eau de toilettes, aftershaves and deodorants.

Moperone (Luvatren, since discontinued) is a typical antipsychotic of the butyrophenone class which is marketed in Japan for the treatment of schizophrenia. It is an antagonist for the D2 (Ki 0.7–1.9 nM), D3 (Ki 0.1–1 nM), and 5-HT2A (Ki 52 nM) receptors. It also has a high binding affinity for the sigma receptors.

Furazabol (, ) (brand names Frazalon, Miotalon, Qu Zhi Shu), also known as androfurazanol, is a synthetic, orally active anabolic-androgenic steroid which has been marketed in Japan since 1969. It is a 17α-alkylated derivative of dihydrotestosterone (DHT) and is closely related structurally to stanozolol, differing from it only by having a furazan ring system instead of pyrazole. Furazabol has a relatively high ratio of anabolic to androgenic activity. As with other 17α-alkylated AAS, it may have a risk of hepatotoxicity. The drug has been described as an antihyperlipidemic and is claimed to b

Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli (Pogostemon cablin). Patchouli oil is an important material in perfumery. The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is obtained industrially from patchouli leaf fermentation.

Metribolone (developmental code R1881, also known as methyltrienolone) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but wa

Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca.

K252a is an alkaloid isolated from Nocardiopsis bacteria. This staurosporine analog is a highly potent cell permeable inhibitor of CaM kinase and phosphorylase kinase (IC50 = 1.8 and 1.7 nmol/L, respectively). At higher concentrations it is also an efficient inhibitor of serine/threonine protein kinases (IC50 of 10 to 30 nmol/L).

2-Methylisoborneol (MIB) is an irregular monoterpene derived from the universal monoterpene precursor geranyl pyrophosphate. MIB and the irregular sesquiterpene geosmin together account for the majority of biologically caused taste and odor outbreaks in drinking water worldwide. MIB has a distinct earthy or musty odor, which most people can easily smell. The odor detection threshold of MIB is very low, ranging from 0.002 to 0.02 micrograms per liter in water. MIB is also a factor in cork taint in winemaking.

chemical compound

Azacyclonol (trade names Ataractan, Calmeran, Frenoton, Frenquel, Psychosan), also known as γ-pipradrol, is a drug which is an ataractive; an agent which diminishes hallucinations in psychotic individuals. It has also been called a tranquilizer and antipsychotic, though these definitions are not accurate as it does not actually possess such properties. Despite being a positional isomer of pipradrol, it is not a psychostimulant, and instead has mild depressant effects.

Quifenadine (, trade name: Fenkarol, Фенкарол) is a 2nd generation antihistamine drug, marketed mainly in post-Soviet countries. Chemically, it is a quinuclidine derivative.

Norelgestromin, or norelgestromine, sold under the brand names Evra and Ortho Evra among others, is a progestin medication which is used as a method of birth control for women. The medication is available in combination with an estrogen and is not available alone. It is used as a patch that is applied to the skin.

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic used mainly in China. It is a derivative of the better-known opioid etorphine, a very potent veterinary painkiller and anesthetic medication used primarily for the sedation of large animals such as elephants, giraffes, and rhinos.

3-Ethyl-3-pentanol, also known as 3-ethylpentan-3-ol, is a tertiary alcohol with the molecular formula C7H16O.