I think it is relatively well known that mesoamericans performed enemas of alcoholic beverages to bypass first-pass metabolism. But they didn't just use alcoholic beverages! They used many plants from Ipomoea violacea, Brugmansia ceratocaula, Banisteriopsis caapi, Anadenanthera peregrina & colubrina, Nicotiana spp, and many others I have no doubt.
Historically enemas were used as medical treatments of hemorrhoids, blood in the stool, constipation, diarrhea, nausea, and others. Enemas were also a large part of shamanic practices, not just in mesoamerica but all over the world! It is well known the egyptians used enemas after observing the ibis, a bird in the family Threskiornithidae which is the symbolic animal of the shamanic god Thoth which supposedly inserts its tube-like beak into its own rectum and gives itself enemas.
I am making this post not just because I find this fascinating, but also because I see many-a-post on this forum and others on stomach complications arising from ingesting substances from opium, to Ipomoea species, ayahuasca, and bufotenin. I feel strongly that if we can first, destigmatize enemas--not that that is really prevalent on this forum
we can then solve some very real, and problematic issues with many drugs. Stomach discomfort ruining a trip, nausea purging the dose before it is absorbed well, and using less substance to achieve an equal level of intoxication.
Now obviously there needs to be some words on safety, because enemas are so efficient at delivering drugs into the bloodstream it can be really easy to over-do it. This isn't necessarily a life-threatening problem with things such as DMT and others, but something like opium or even coffee could potentially put one at serious risk. Plants like Anadenanthera's and Ipomoea's could have other alkaloids and terpenes which could potentially cause issues, however they do have a history of human use which means something I think (granted Brugmansia and Datura have also been used). Enemas also have the problem of dehydrating the individual and imbalancing mineral content of one's body, sometimes to a lethal degree. You should ALWAYS drink a glass or two of water before performing and enema. Try and use sterilized distilled water, although it isn't necessary it will help prevent potential infections or radical changes in your mineral levels. Never use high or low pH fluids or other caustic liquids to avoid causing tissue damage to your colon and rectum.
I think that there is MUCH work to be done here, and many many new discoveries awaiting!!! The entheogenic value of a plant may present itself at one ROA (i.e. snuffing yopo/cebil or oral Ipomoea seed) however rectal absorption could greatly help and reduce nausea and stomach discomfort. More importantly I think, rectal could really be a method which brings out the spirit of a plant because of increased dose and the bypassing of first-pass metabolism. A plant which comes to my mind is Acorus calamus.